tert-Butyldimethylsilyl chloride → (2S,4R)-4-(tert-butyldimethylsilyloxy)-4-(3-bromophenyl)-2-methyltetrahydropyran

HRID 2260629Notes

Reaction equation

HRID 2260629 reaction equation
[OH:1][C@:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=2)[CH2:7][CH2:6][O:5][C@@H:4]([CH3:8])[CH2:3]1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>>[Si:16]([O:1][C@:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=2)[CH2:7][CH2:6][O:5][C@@H:4]([CH3:8])[CH2:3]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

3

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 54527261(2S,4R)-4-hydroxy-4-(3-bromophenyl)-2-methyltetrahydropyran

Product 1

HCID 54104922(2S,4R)-4-(tert-butyldimethylsilyloxy)-4-(3-bromophenyl)-2-methyltetrahydropyranYield 78%

Procedure

Using an analogous procedure to that described in the portion of Example 18 which is concerned with the preparation of starting materials, the 4-(3-bromophenyl)-2-methyltetrahydropyran so obtained was reacted with tert-butyldimethylsilyl chloride to give (2S,4R)-4-(tert-butyldimethylsilyloxy)-4-(3-bromophenyl)-2-methyltetrahydropyran in 78% yield as an oil.

Workup

  1. customis concerned with the preparation of starting materials

Sources & evidence

ORD record
ord-987e7520a6be4a878eedb4a614c07e99
Source dataset
uspto-grants-1995_12
Patent number
US05478842

Reaction notes

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