Imidazole → 5-t-Butyldimethylsilyloxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2308872Notes

Reaction equation

[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[OH:14][C:15]1[C:16]([CH3:30])=[C:17]([CH3:29])[C:18]2[O:22][CH:21]([CH2:23][CH2:24][CH2:25][I:26])[S:20][C:19]=2[C:27]=1[CH3:28].O>C1C=CC=CC=1>[Si:1]([O:14][C:15]1[C:16]([CH3:30])=[C:17]([CH3:29])[C:18]2[O:22][CH:21]([CH2:23][CH2:24][CH2:25][I:26])[S:20][C:19]=2[C:27]=1[CH3:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

5.2 g of t-butyldimethylsilyl chloride and 4.6 g of imidazole were dissolved in 80 ml of benzene, and then the reaction mixture was heated for 1 hour at 50° C., after which a solution of 6.3 g of 5-hydroxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Examples 74 and 75) in 10 ml of benzene was added and the reaction mixture was allowed to react for 8 hours at 40°-45° C. The reaction product was cooled, poured into water, and then extracted with benzene. The extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography and the title compound was obtained from the fraction eluted with a 9:1 by volume mixture of cyclohexane and benzene.

Workup

customto react for 8 hours at 40°-45° C
temperatureThe reaction product was cooled
extractionextracted with benzene
washThe extract was washed with water
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-b840f6760de445b685d08e2731b1f28c
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04691027

Reaction notes

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