1,3-Dibromobenzene → (2S,4R)-4-hydroxy-4-(3-bromophenyl)-2-methyltetrahydropyran

HRID 1721691Notes

Reaction equation

HRID 1721691 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[CH3:9][C@H:10]1[CH2:15][C:14](=[O:16])[CH2:13][CH2:12][O:11]1>>[OH:16][C@:14]1([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=2)[CH2:13][CH2:12][O:11][C@@H:10]([CH3:9])[CH2:15]1

Participants

3

Reactant 2

HCID 79271,3-DibromobenzeneHCID 10125057(2S)-2-Methyloxan-4-one

Product 1

HCID 54527261(2S,4R)-4-hydroxy-4-(3-bromophenyl)-2-methyltetrahydropyranYield 66%

Procedure

Using an analogous procedure to that described in the portion of Example 6 which is concerned with the preparation of starting materials, 1,3-dibromobenzene was reacted with (2S)-2-methyltetrahydropyran-4-one to give (2S,4R)-4-hydroxy-4-(3-bromophenyl)-2-methyltetrahydropyran in 66% yield as an oil.

Sources & evidence

ORD record
ord-604effa6f20b4c37842cea80fe4ada89
Source dataset
uspto-grants-1996_04
Patent number
US05512594

Reaction notes

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