Water → HCID 21459470, compound

HRID 1941028Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH:2]1[CH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18]O)[CH2:13][CH2:12]1.CCN(S(F)(F)[F:26])CC.O>ClCCl>[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH:2]1[CH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][F:26])[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

The above 2-(4-(1,4-dioxaspiro[4.5]decyl)cyclohexyl)ethanol (20 g, 70.8 mmol) was dissolved in dichloromethane (70 ml), followed by dropwise adding to the solution, DAST (13 g, 80.7 mmol), stirring at 0° C. for one hour, adding water to the reaction solution, washing the resulting organic layer successively with a saturated aqueous solution of sodium bicarbonate and water, distilling off the solvent, purifying the residue according to column chromatography using heptane/ethyl acetate as a developing solvent, on silica gel, to obtain 1-(4-(1,4-dioxaspiro[4,5]decyl)cyclohexyl)-2-fluoroethane, adding thereto formic acid (80 ml), refluxing the mixture for 2 hours, extracting the resulting product with toluene, washing the extraction solution successively with a saturated aqueous solution of sodium bicarbonate, distilling off the solvent, to isolate 4-(4-(2-fluoroethyl)cyclohexyl)cyclohexanone (8.0 g, 35.3 mmol). The yield of this product from 2-(4-(1,4-dioxaspiro[4,5]decyl)cyclohexyl)ethanol was 49.9%.

Workup

washwashing the resulting organic layer successively with a saturated aqueous solution of sodium bicarbonate and water
distillationdistilling off the solvent
custompurifying the residue

Sources & evidence

ORD record: ord-c32ab3997d5f4d3798b79f48f9acfb18
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05702641

Reaction notes

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