Water → 3-Buten-2-ol, 1-(triphenylmethoxy)-, (2S)-

HRID 1524638Notes

Reaction equation

[Li][CH2:2]CCC.[I-].C[S+](C)C.[CH2:11]([O:15][C:16](C1C=CC=CC=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:12]1[O:14][CH2:13]1.O.[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C1COCC1>[C:16]([O:15][CH2:11][C@@H:12]([OH:14])[CH:13]=[CH2:2])([C:38]1[CH:37]=[CH:36][CH:41]=[CH:40][CH:39]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of n-BuLi in hexane (2.6 M; 182 mL) was added dropwise to a solution of trimethylsulfonium iodide (96.8 g) in THF (800 mL) at −30° C. After stirring at −20° C. for 20 min, (S)-trityl glycidyl ether (50.0 g) was added at the same temperature, and the mixture was stirred at RT for 30 min. Water was added to the reaction solution, followed by extraction with diethyl ether. The organic layer was dried over anhydrous MgSO4. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (52.0 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 3.09-3.13 (m, 1H), 3.20-3.23 (m, 1H), 4.26-4.29 (m, 1H), 5.14-5.32 (m, 2H), 5.76-5.84 (m, 1H), 7.23-7.45 (m, 15H).

Workup

stirringthe mixture was stirred at RT for 30 min
extractionfollowed by extraction with diethyl ether
dry with materialThe organic layer was dried over anhydrous MgSO4
customThe insoluble matter was separated by filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-f7ecd8de211f4c9392882321ae70bc08
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079914B2

Reaction notes

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