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Water → Ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-7-hydroxyheptanoate

HRID 1921878
Notes
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Reaction equation

HRID 1921878 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[C:16]([F:32])[CH:15]=1)[C:10](O)=[O:11])[CH3:2].O>C1COCC1>[F:32][C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([F:20])[C:17]=1[O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:23]([CH3:25])[CH3:24])[CH:26]([CH3:28])[CH3:27])[CH2:13][CH:9]([CH2:10][OH:11])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 962WaterHCID 579719032-(3,5-Difluoro-4-triisopropylsilanyloxybenzyl)heptanedioic acid 7-ethyl ester

Product 1

HCID 57971930Ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-7-hydroxyheptanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

1.6 g (3.29 mmol) of 2-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)heptanedioic acid 7-ethyl ester are dissolved in 30 ml of THF and cooled to −10° C. under argon. Then, 4.27 ml (4.27 mmol) of a 1 M borane-THF complex solution are added dropwise, and the mixture is stirred at 0° C. until reaction is complete. The mixture is hydrolyzed with water and extracted with ethyl acetate, and the combined organic phases are concentrated. The resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1, 3:1). 1.18 g (76% of theory) of the title compound are obtained.

Workup

  1. additionThen, 4.27 ml (4.27 mmol) of a 1 M borane-THF complex solution are added dropwise
  2. extractionextracted with ethyl acetate
  3. concentrationthe combined organic phases are concentrated
  4. customThe resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1, 3:1)

Sources & evidence

ORD record
ord-a2f73c2c3a684f0283439687cbbeba30
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173704B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes