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Chloromethyl Methyl Ether → HCID 71499446, compound

HRID 633665
Notes
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Reaction equation

HRID 633665 reaction equation
[OH:1][C@@H:2]1[C@@:9]([CH3:16])([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C@@H:8]2[C:17](=[O:18])[C@@:4]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])([C:5]([O:20][CH3:21])=[CH:6][C:7]2=[O:19])[CH2:3]1.[CH3:27][O:28][CH2:29]COC.C(N(C(C)C)CC)(C)C.COCCl>CCCCCC>[CH3:21][O:20][C:5]1[C@:4]2([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[C:17](=[O:18])[C@@H:8]([C@:9]([CH3:16])([CH2:10][CH2:11][CH:12]=[C:13]([CH3:14])[CH3:15])[C@@H:2]([O:1][CH2:27][O:28][CH3:29])[CH2:3]2)[C:7](=[O:19])[CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 80711,2-DimethoxyethaneHCID 81531DiisopropylethylamineHCID 86718445HCID 86718445, compound

Product 1

HCID 71499446HCID 71499446, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8058
Hexane
Solvent

Conditions

Temperature
60 °C

Procedure

A flame-dried round-bottom flask under argon atmosphere is charged with 458 mg (1.22 mmol, 1 equiv.) of starting material 20, 1.3 mL 1,2-dimethoxyethane, and 953 μL (5.34 mmol, 5.5 equiv.) diisopropylethylamine. With stirring, 376 μL (4.95 mmol, 5.1 equiv.) methoxymethyl chloride is added dropwise. The stirring reaction is heated to 60° C. for four hours before being allowed to cool to room temperature. Once the reaction has cooled, it is transferred to a separatory funnel in 50 mL hexane and the organic layer is washed sequentially with 10% aqueous hydrochloric acid, water, and brine. The organic solution is then dried with MgSO4 and concentrated in vacuo to give a clear to yellow oil. The crude product is purified by silica gel chromatography (Rf=0.25 in 4:1 hexane:ethyl acetate) to give 380 mg (97% yield) of 50 as a clear oil. 1H NMR (500 MHz, CDCl3) δ ppm 5.67 (s, 1H), 5.07 (tt, J=7.1, 1.4 Hz, 1H), 4.97 (tt, J=6.2, 1.3 Hz, 1H), 4.58 (dd, J=36.8, 7.0 Hz, 2H), 3.75 (s, 3H), 3.60 (dd, J=11.2, 5.5 Hz, 1H), 3.32 (s, 3H), 3.18 (s, 3H), 2.48 (dd, J=14.4, 6.2 Hz, 1H), 2.29-2.42 (m, 2H), 2.21 (dd, J=13.4, 5.4 Hz, 3H), 1.87 (ddt, J=18.3, 12.1, 5.5, 5.5 Hz, 3H), 1.78 (dd, J=13.3, 11.4 Hz, 3H), 1.65 (s, 12H), 1.57 (ddd, J=12.9, 4.6 Hz, 1H), 1.27 (ddd, J=12.9, 4.5 Hz, 1H), 0.92 (s, 3H). 13C NMR (126 MHz, CDCl3) δ ppm 205.2, 193.0, 177.3, 134.3, 131.8, 124.3, 119.1, 106.0, 97.1, 77.4, 76.9, 69.2, 57.1, 55.9, 55.8, 46.3, 37.6, 37.4, 29.6, 26.0, 25.9, 21.6, 18.1, 17.8, 16.5. HRMS-ESI (m/z): [M+H]+ calculated for C24H36O5, 405.2636. found 405.2637.

Workup

  1. customThe stirring reaction
  2. temperatureto cool to room temperature
  3. temperatureOnce the reaction has cooled
  4. washthe organic layer is washed sequentially with 10% aqueous hydrochloric acid, water, and brine
  5. dry with materialThe organic solution is then dried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a clear to yellow oil
  8. customThe crude product is purified by silica gel chromatography (Rf=0.25 in 4:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-b068dae4de3c4ea683bd192559d9d71d
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321713B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes