Water → (5R)-5-[(trityloxy)methyl]-2,2-divinyltetrahydrofuran

HRID 2300157Notes

Reaction equation

[C:1]([O:20][CH2:21][C@@H:22]([OH:31])[CH2:23][CH2:24][C:25]([CH:29]=[CH2:30])(O)[CH:26]=[CH2:27])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C(S(Cl)(=O)=O)=CC=CC=1.O>N1C=CC=CC=1>[C:1]([O:20][CH2:21][C@@H:22]1[O:31][C:25]([CH:26]=[CH2:27])([CH:29]=[CH2:30])[CH2:24][CH2:23]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

13.0 g of (2S)-1-(trityloxy)-5-vinyl-6-heptene-2,5-diol and 57.2 g of toluenesulfonyl chloride were dissolved in 200 ml pyridine, and stirred at 80° C. overnight. After the reaction was completed, water was added thereto, and it was stirred at room temperature for 10 min. After extracting twice with ethyl acetate, washed with brine, and dried over magnesium sulfate. The solvent was removed, and the resulting residue was dissolved in toluene. After the solvent was removed again, the resulting residue was purified by silica gel column chromatography to give 5.88 g of (5R)-5-[(trityloxy)methyl]-2,2-divinyltetrahydrofuran.

Workup

stirringit was stirred at room temperature for 10 min
extractionAfter extracting twice with ethyl acetate
washwashed with brine
dry with materialdried over magnesium sulfate
customThe solvent was removed
dissolutionthe resulting residue was dissolved in toluene
customAfter the solvent was removed again
customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-1af204d9c33942568250f85f793dcf5f
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498159B1

Reaction notes

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