Hydrogen Peroxide → HCID 178455703, compound

HRID 1765010Notes

Reaction equation

C1C[O:4]CC1.[CH2:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]([CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[C:17]([F:25])[C:18]([F:24])=[CH:19][CH:20]=3)[O:15]2)[CH2:10][CH2:9]1)[CH3:7].C([Li])CCC.CCCCCC.OO>O.C(O)(=O)C>[CH2:6]([C@H:8]1[CH2:9][CH2:10][C@H:11]([CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[C:17]([F:25])[C:18]([F:24])=[C:19]([OH:4])[CH:20]=3)[O:15]2)[CH2:12][CH2:13]1)[CH3:7]

Participants

Conditions

Temperature: -50 °C

Procedure

Into the THF (150 ml) solution of 2-(trans-4-ethylcyclohexyl)-7,8-difluorochroman (28 g), a 1.6 M butyllithium-hexane solution (65 ml) was added dropwise at −60° C., and stirred for 2 hours at −50° C. Into this, borate trimethyl (15 g) was added dropwise, stirred for 30 minutes, and warmed to 0° C. over 2 hours. Into this, acetic acid (10 ml) was added, and stirred for 20 minutes, to which 30% hydrogen peroxide aqueous solution (20 ml) was gradually added, and stirred for 1 hour. Into this, water (100 ml) was added, which was subjected to extraction using ethyl acetate, followed by concentration. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 2-(trans-4-ethylcyclohexyl)-7,8-difluoro-6-hydroxychroman (28 g).

Workup

stirringstirred for 30 minutes
temperaturewarmed to 0° C. over 2 hours
additionwas gradually added
stirringstirred for 1 hour
extractionwhich was subjected to extraction
concentrationfollowed by concentration
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-d229fed9875d45f986cf4d5bfff344d1
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226644B2

Reaction notes

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