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Tetrabutylammonium Fluoride → Tert-butyl 4-(cis-3-hydroxycyclohexyl)-2,2-dimethylbutyrate

HRID 347422
Notes
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Reaction equation

HRID 347422 reaction equation
[Si]([O:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][C@H:21]([CH2:25][CH2:26][C:27]([CH3:36])([CH3:35])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][C@H:21]([CH2:25][CH2:26][C:27]([CH3:36])([CH3:35])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69241608Tert-butyl 4-[cis-3-(tert-butyldiphenylsilanyloxy)cyclohexyl]-2,2-dimethylbutyrate

Product 1

HCID 69244301Tert-butyl 4-(cis-3-hydroxycyclohexyl)-2,2-dimethylbutyrate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

2 g of tert-butyl 4-[cis-3-(tert-butyl-diphenylsilanyloxy)cyclohexyl]-2,2-dimethylbutyrate are dissolved in 10 ml of tetrahydrofuran, and 8 ml of a 1 M solution of tetrabutylammonium fluoride and tetrahydrofuran are added. The mixture is stirred at 60° C. for 2 hours. The reaction mixture is concentrated under reduced pressure and purified on silica gel using the mobile phase n-heptane:ethyl acetate=20:1=>1:1. This gives 730 mg of tert-butyl 4-[cis-3-hydroxycyclohexyl)-2,2-dimethylbutyrate as an oil. C16H30O3 (270.42), Rf(n-heptane:ethyl acetate=5:1)=0.22.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. custompurified on silica gel using the mobile phase n-heptane

Sources & evidence

ORD record
ord-8ac0bfc15c5144e28c19bb52c7e56ac5
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07173151B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes