Triethylamine → HCID 14127517, compound

HRID 2291291Notes

Reaction equation

[C:1]([Cl:4])(Cl)=[S:2].[OH:5][C:6]1[CH:31]=[CH:30][C:9]([C:10]([O:12][Si:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:11])=[CH:8][CH:7]=1.C(N(CC)CC)C>C(OCC)C>[Cl:4][C:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][Si:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:11])=[CH:30][CH:31]=1)=[S:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 40.7 ml of thiophosgene in 300 ml of dry diethyl ether at -78° C. was added dropwise a solution of 20 g of diphenyl-(2-methylprop-2-yl)silyl 4-hydroxybenzoate and 8.5 ml of triethylamine. After having been stirred for a further 30 minutes at -78° C. and 90 minutes at room temperature, the mixture was partitioned between diethyl ether and water. The organic layer was washed with water and brine, was dried over calcium chloride, and then evaporated in vacuo to afford 25.9 g of an orange oil. Crromatography over silica gel and elution with hexane-ethyl acetate mixtures afforded 16.8 g of the title compound.

Workup

customthe mixture was partitioned between diethyl ether and water
washThe organic layer was washed with water and brine
dry with materialwas dried over calcium chloride
customevaporated in vacuo

Sources & evidence

ORD record: ord-e9d440a675074c38ad735e1f3ed491c8
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04795748

Reaction notes

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