Hydrochloric Acid → 4-(Adamantan-1-ylmethoxy)-5-(1-((tert-butyldimethylsilyl)oxy)ethyl)-2-fluorobenzoic acid

HRID 1849736Notes

Reaction equation

HRID 1849736 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[C:22]([CH:23]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH3:24])=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[C:15]([F:33])[CH:14]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.[OH-].[Li+].Cl>O1CCCC1.O>[C:1]12([CH2:11][O:12][C:13]3[C:22]([CH:23]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])[CH3:24])=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[C:15]([F:33])[CH:14]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86703613Methyl 4-(adamantan-1-ylmethoxy)-5-(1-((tert-butyldimethylsilyl)oxy)-ethyl)-2-fluorobenzoate

Product 1

HCID 867036144-(Adamantan-1-ylmethoxy)-5-(1-((tert-butyldimethylsilyl)oxy)ethyl)-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(adamantan-1-ylmethoxy)-5-(1-((tert-butyldimethylsilyl)oxy)-ethyl)-2-fluorobenzoate in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide monohydrate (0.151 g, 3.6 mmol) in water (5 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 2 days. After adjusting the reaction mixture to pH 5 with 1 N hydrochloric acid, the mixture was extracted with dichloromethane (3×20 mL). The combined organic phase was washed with brine (5 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo yielded the title compound as a yellowish oil (0.33 g, quant.), which was used without further purification: MS (ES+) m/z 461.4 (M−1).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×20 mL)
  2. washThe combined organic phase was washed with brine (5 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-4bd6ce525eb24a8f923d593bf41d8d46
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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