Water → HCID 20034699, compound

HRID 231195Notes

Reaction equation

[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH2:2]1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:19][CH3:20])[C:16]=1[O:17][CH3:18])[CH2:12]Cl.O>O1CCCC1.CCCCC>[CH3:20][O:19][C:15]1[CH:14]=[C:11]([CH2:12][CH:2]2[S:3][CH2:4][CH2:5][CH2:6][S:1]2)[CH:10]=[C:9]([O:8][CH3:7])[C:16]=1[O:17][CH3:18]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 26.7 g of 1,3-dithiane in 222 ml of tetrahydrofuran which has been cooled to -78° C. was added over a period of 15 minutes, 137 ml of 1.7M solution of tetra-butyl lithium in pentane. The resultant mixture was then stirred for 45 minutes, while maintaining the temperature at -78° C., after which time it was warmed to 0° C. The mixture was then added to an ice-cold solution of 48.0 g of 3,4,5-trimethoxybenzyl chloride in 222 ml of tetrahydrofuran over a period of 20 minutes, after which time it was stirred for an additional 90 minutes at 0° C. 50 ml of water was then carefully added and the tetrahydrofuran was removed by evaporation at a temperature below 40° C. The resultant white slurry was then extracted with a mixture of methylene chloride and water. The organic layer was then evaporated and the crude product was washed with petroleum ether to yield a white solid.

Workup

additionwas added over a period of 15 minutes
temperatureafter which time it was warmed to 0° C
customthe tetrahydrofuran was removed by evaporation at a temperature below 40° C
extractionThe resultant white slurry was then extracted with a mixture of methylene chloride and water
customThe organic layer was then evaporated
washthe crude product was washed with petroleum ether
customto yield a white solid

Sources & evidence

ORD record: ord-af5b920c12804beb8d077589c36fa15d
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845129

Reaction notes

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