Methanol → HCID 10894748, compound

HRID 857962Notes

Reaction equation

[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C@H:8]([CH3:24])[C@@H:9]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C@@H:10]([CH3:13])[CH:11]=O)([CH3:4])[CH3:3].Br[CH:28]([Si](C)(C)C)[CH:29]=[CH2:30].CO.[OH-].[K+]>C1COCC1>[CH3:1][C:2]([Si:5]([O:6][CH2:7][C@H:8]([CH3:24])[C@@H:9]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)[C@@H:10]([CH3:13])/[CH:11]=[CH:30]\[CH:29]=[CH2:28])([CH3:26])[CH3:25])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension consisting of CrCl2 (12.93 g, 105.38 mmol) and 700 mL anhydrous THF is cooled to 0° C. 2,4-dideoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-3-O-[(4-methoxyphenyl)methyl]-2,4-dimethyl-L-lyxose (8.9 g, 23.42 mmol) in 40 mL THF is added dropwise. (1-Bromoallyl) trimethylsilane (22.61, 117.1 mmol) is added neat. After 3 h at room temperature, the reaction mixture is cooled to 10° C. Methanol (270 mL) and 6 N aqueous KOH (550 mL) are added in sequence, keeping the reaction temperature less than 20° C. during the addition. The mixture is stirred overnight at room temperature. The organic layer is separated. The aqueous layer is extracted with ether (3×400 mL). The combined organic phase is washed with brine, dried over NaSO4, and concentrated. Flash chromatography gives the desired compound (6.74 g, 71.2%) as a clear oil.

Workup

temperaturethe reaction mixture is cooled to 10° C
customthe reaction temperature less than 20° C.
additionduring the addition
customThe organic layer is separated
extractionThe aqueous layer is extracted with ether (3×400 mL)
washThe combined organic phase is washed with brine
dry with materialdried over NaSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-86c7dafe7d224eceb696cd236bf420d3
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148218B2

Reaction notes

Loading…