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Water → Ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(methoxymethyloxy)-naphth-7-yl]naphth-2-oate

HRID 1379
Notes
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Reaction equation

HRID 1379 reaction equation
C[C:2]1(C)[CH2:11][CH2:10][CH:9](O)[C:8]2[CH:7]=[C:6]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[CH:19]=[C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:17]=[CH:16]4)[CH:5]=C[C:3]1=2.CCN([CH:35]([CH3:37])[CH3:36])C(C)C.[CH3:38][O:39][CH2:40]Cl.[I-].C([NH3+])(C)(C)C.[OH2:48]>C(Cl)Cl.C(OCC)(=O)C>[CH2:26]([O:25][C:23]([C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([CH:6]3[CH:7]([O:48][CH2:40][O:39][CH3:38])[C:8]4[CH:3]=[CH:2][CH:11]=[CH:10][C:9]=4[C:35]([CH3:36])([CH3:37])[CH2:5]3)[CH:14]=2)[CH:19]=1)=[O:24])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 15462839Ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxynaphth-2-yl]naphth-2-oate2×HCID 22344722t-Butylammonium Iodide

Product 1

HCID 22571528
Ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(methoxymethyloxy)-naphth-7-yl]naphth-2-oate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (0° C.) solution of 130 mg (0.35 mmol) of ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(hydroxy)-naphth-7-yl]naphth-2-oate (Compound B4) in 2.0 mL of methylene chloride was added 50 mg (0.15 mL, 0.86 mmol) of Hunig's base, followed by 0.21 g (0.20 mL, 2.6 mmol) chloromethyl methyl ether was added and stirred at room temperature for 14 h. About 500 mgs of t-butylammonium iodide was then added and the reaction was warmed to 35° C. for one additional hour. The reaction was diluted with water, and extracted with CH2Cl2 (2×). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an off. The title compound was obtained as an oil after flash chromatography (silica, 10% ethyl acetate).

Workup

  1. additionwas added
  2. temperaturethe reaction was warmed to 35° C. for one additional hour
  3. extractionextracted with CH2Cl2 (2×)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give an off

Sources & evidence

ORD record
ord-13e57f77780b42eab24c40acb5fbde1d
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723666

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes