Chloromethyl Methyl Ether → HCID 59858077, compound

HRID 254238Notes

Reaction equation

HRID 254238 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1([CH3:22])[CH2:15][CH2:14][C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH:17]([CH2:18][CH2:19]4)[C:10]3=[C:11]([OH:16])[CH:12]=2)[O:7]1.C(N(C(C)C)CC)(C)C.[CH3:33][O:34][CH2:35]Cl>C(Cl)Cl.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1([CH3:22])[CH2:15][CH2:14][C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH:17]([CH2:18][CH2:19]4)[C:10]3=[C:11]([O:16][CH2:33][O:34][CH3:35])[CH:12]=2)[O:7]1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 11716671HCID 11716671, compound

Product 1

HCID 59858077HCID 59858077, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-(6-hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propionic acid methyl ester from Example 13 (400 mg, 1.27 mmol) and diisopropyl ethylamine (DIPEA) (0.90 ml, 5 mmol) in 4 mL of DCM was slowly added chloromethyl methyl ether (0.30 mL, 3.8 mmol) at room temperature. The reaction was left over night. After the completion of reaction shown by TLC, the mixture was poured into brine and the organic layer was separated and dried over MgSO4. After the removal of solvents the residue was purified through flash column chromatography on silica gel (25% of ethyl acetate in hexane) to afford 340 mg of 3-(6-methoxymethoxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propionic acid methyl ester. 1H-NMR (300 MHz, CDCl3) δ (ppm)): 6.25 (s, 1H), 4.29 (s, 1H), 3.63 (s, 3H), 3.48 (s, 1H), 3.40 (s, 1H), 2.66-2.64 (m, 2H), 2.47-2.43 (m, 2H), 1.83-1.50, (m, 12H) 1.18 (s, 3H).

Workup

  1. customat room temperature
  2. waitThe reaction was left over night
  3. customAfter the completion of reaction
  4. customthe organic layer was separated
  5. dry with materialdried over MgSO4
  6. customAfter the removal of solvents the residue
  7. customwas purified through flash column chromatography on silica gel (25% of ethyl acetate in hexane)

Sources & evidence

ORD record
ord-38264c46038d4f548a55323b3909c51a
Source dataset
uspto-grants-2011_01
Patent number
US07875607B2

Reaction notes

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