HCID 86589619, compound → HCID 86596983, compound

HRID 1723916Notes

Reaction equation

[CH3:1][C:2]12[CH:11]([CH:12]=[O:13])[CH2:10][CH2:9][CH:8]=[C:7]1[CH2:6][C:5]1([S:17][CH2:16][CH2:15][S:14]1)[CH2:4][CH2:3]2.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH3:1][C:2]12[CH:11]([CH:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[OH:13])[CH2:10][CH2:9][CH:8]=[C:7]1[CH2:6][C:5]1([S:14][CH2:15][CH2:16][S:17]1)[CH2:4][CH2:3]2

Participants

Conditions

Temperature: -78 °C

Procedure

Aldehyde 241 (200 mg, 0.746 mmol) was dissolved in 10 mL THF and cooled to −78° C. Phenylmagnesium bromide (1M in THF, 1.12 mL, 1.12 mmol) was added to the solution dropwise and the mixture was allowed to warm to room temperature over 2 hours. The reaction mixture was then cooled to 0° C. and quenched with 10 mL of water. The layers were separated and the aqueous layer was extracted with (3×10 mL) ether. The pooled organic extracts was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. Purification by flash chromatography over silica gel (10% ethyl acetate-hexanes) afforded alcohol 247 (240 mg, 93%) as a white solid.

Workup

temperatureto warm to room temperature over 2 hours
temperatureThe reaction mixture was then cooled to 0° C.
customquenched with 10 mL of water
customThe layers were separated
extractionthe aqueous layer was extracted with (3×10 mL) ether
washThe pooled organic extracts was washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under vacuum
customPurification by flash chromatography over silica gel (10% ethyl acetate-hexanes)

Sources & evidence

ORD record: ord-eda68725f5744489acfddc239072bba7
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485660B2

Reaction notes

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