Water → HCID 20034704, compound

HRID 231196Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][CH:14]2[S:19][CH2:18][CH2:17][CH2:16][S:15]2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C([Li])(C)(C)C.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[CH2:30]Cl.O>O1CCCC1.CCCCC>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([CH2:13][C:14]2([CH2:30][C:29]3[CH:32]=[C:33]([O:37][CH3:38])[C:34]([O:35][CH3:36])=[C:27]([O:26][CH3:25])[CH:28]=3)[S:15][CH2:16][CH2:17][CH2:18][S:19]2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 46.3 g of the compound prepared in (a) above in 230 ml of tetrahydrofuran at 0° C. was added, over a period of 20 minutes, 99.6 ml of a 1.7M solution of tert.-butyl lithium in pentane. The resultant mixture was then stirred for 20 minutes, after which time 34.9 g of 3,4,5-trimethoxybenzyl chloride in 150 ml of tetrahydrofuran at 0° C. was added over a period of 15 minutes. The reaction mixture was then stirred for 45 minutes, while the temperature was maintained at 0° C., and then 100 ml of water was carefully added. The resultant slurry was then extracted with a mixture of ethyl acetate and water and dried. The organic layer was then evaporated and the crude product was washed with diethyl ether to yield a solid.

Workup

additionwas added, over a period of 20 minutes
extractionThe resultant slurry was then extracted with a mixture of ethyl acetate and water
customdried
customThe organic layer was then evaporated
washthe crude product was washed with diethyl ether
customto yield a solid

Sources & evidence

ORD record: ord-1516b1a664f343ee9c6d39c4f149a24a
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845129

Reaction notes

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