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

HRID 2350994
Notes
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Reaction equation

HRID 2350994 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 135920605-Hydroxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Product 1

HCID 148021855-t-Butyldimethylsilyloxy-2-(3-iodopropyl)-4,6,7-trimethyl-1,3-benzoxathiole

Reagents, catalysts & solvents 1

HCID 241
Benzene
Solvent
2×

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

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

Sources & evidence

ORD record
ord-76dc0d40ef34427fa255da9570c6245e
Source dataset
uspto-grants-1989_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04871762

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes