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Tetrabutylammonium Fluoride → Tert-butyl 2-(cis-3-hydroxycyclohexylmethoxy)-2-methylpropionate

HRID 854649
Notes
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Reaction equation

HRID 854649 reaction equation
[Si]([O:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][C@H:21]([CH2:25][O: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>C(#N)C>[OH:18][C@@H:19]1[CH2:24][CH2:23][CH2:22][C@H:21]([CH2:25][O: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 69243064Tert-butyl 2-[cis-3-(tert-butyldiphenylsilanyloxy)cyclohexylmethoxy]-2-methylpropionate

Product 1

HCID 67214679Tert-butyl 2-(cis-3-hydroxycyclohexylmethoxy)-2-methylpropionate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

16 g of tert-butyl 2-[cis-3-(tert-butyldiphenylsilanyloxy)cyclohexylmethoxy]-2-methylpropionate are dissolved in 100 ml of acetonitrile, and 62 ml of tetrabutylammonium fluoride (1 N solution in tetrahydrofuran) are added. After 2 h of stirring at 60° C., the reaction has ended and the mixture is concentrated under reduced pressure. The residue is extracted from water/ethyl acetate. The combined org. phases are extracted with saturated sodium chloride solution and dried over magnesium sulfate, and the solvent is removed under reduced pressure. The crude product is purified on silica gel (heptane/ethyl acetate 15:1→1:1). This gives 16 g of the product tert-butyl 2-(cis-3-hydroxycyclohexylmethoxy)-2-methylpropionate as a colorless oil.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. extractionThe residue is extracted from water/ethyl acetate
  3. extractionphases are extracted with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customThe crude product is purified on silica gel (heptane/ethyl acetate 15:1→1:1)

Sources & evidence

ORD record
ord-923243641a254aeca9b543f8c1a1d3bf
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259177B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes