Water → Tert-butyl 2-[cis-3-hydroxymethylcyclohexylmethoxy]-2-methylpropionate

HRID 854663Notes

Reaction equation

[Si]([O:8][CH2:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([CH2:16][O:17][C:18]([CH3:27])([CH3:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11]1)(C(C)(C)C)(C)C.O.CC(OC)(C)C>C1COCC1>[OH:8][CH2:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][C@H:12]([CH2:16][O:17][C:18]([CH3:27])([CH3:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11]1

Participants

Conditions

Temperature: 60 °C

Procedure

4.5 g of tert-butyl 2-[cis-3-(tert-butyidimethylsilanyloxymethyl)cyclohexyl-methoxy]-2-methylpropionate (synthesis analogously to tert-butyl 2-[cis-3-(tert-butyldimethylsilanyloxymethyl)cyclohexylmethoxy]-2-methylpropionate in Example 55) are dissolved in 85 ml of THF, 2.24 g of TBAF trihydrate are added and the mixture is stirred at 60° C. for 90 min. Water and MTBE are added, the phases are separated and the organic phase is dried over MgSO4 and concentrated. The residue is chromatographed on silica gel (heptane/ethyl acetate 1:1), which gives 1.45 g of tert-butyl 2-[cis-3-hydroxymethylcyclohexylmethoxy]-2-methylpropionate. C16H30O4 (286.42), MS (ESI): 287 (MH+).

Workup

customthe phases are separated
dry with materialthe organic phase is dried over MgSO4
concentrationconcentrated
customThe residue is chromatographed on silica gel (heptane/ethyl acetate 1:1), which

Sources & evidence

ORD record: ord-54b1152ae3c040b1a3eab6de9a3ac3de
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259177B2

Reaction notes

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