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

HRID 854649Notes

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

Participants

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

concentrationthe mixture is concentrated under reduced pressure
extractionThe residue is extracted from water/ethyl acetate
extractionphases are extracted with saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customthe solvent is removed under reduced pressure
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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