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Tetrabutylammonium Fluoride → Tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)but-2-enoate

HRID 347416
Notes
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Reaction equation

HRID 347416 reaction equation
[Si]([O:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][C@H:21]([CH2:25][CH:26]=[C:27]([CH2:35][CH3:36])[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>[CH2:35]([C:27](=[CH:26][CH2:25][C@H:21]1[CH2:22][CH2:23][CH2:24][C@@H:19]([OH:18])[CH2:20]1)[C:28]([O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[O:29])[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69494093Tert-butyl 4-[cis-3-(tert-butyl-diphenylsilanyloxy)cyclohexyl]-2-ethylbut-2-enoate

Product 1

HCID 69494094Tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)but-2-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

1.3.11 g of tert-butyl 4-[cis-3-(tert-butyl-diphenylsilanyloxy)cyclohexyl]-2-ethylbut-2-enoate are dissolved in 20 ml of tetrahydrofuran, and 15.7 ml of a 1M solution of tetrabutylammonium fluoride in 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=30:1=>ethyl acetate. This gives 1.65 g of tert-butyl 2-ethyl4-(cis-3-hydroxycyclohexyl]but-2-enoate as an oil. C16H28O3 (268.40), Rf(n-heptane:ethyl acetate=5:1)=0.07.

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-dc9f5315e4364295a6ae59d61e4497ed
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