Hydrochloric Acid → (2RS,4SR)-4-(3-benzyloxyphenyl)-4-hydroxy-2-methyltetrahydropyran

HRID 2372477Notes

Reaction equation

HRID 2372477 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][CH:17]1[CH2:22][C:21](=[O:23])[CH2:20][CH2:19][O:18]1.Cl>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:21]2([OH:23])[CH2:20][CH2:19][O:18][CH:17]([CH3:16])[CH2:22]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 27566381-(Benzyloxy)-3-bromobenzeneHCID 103744342-Methyltetrahydro-4H-pyran-4-one

Product 1

HCID 20081957(2RS,4SR)-4-(3-benzyloxyphenyl)-4-hydroxy-2-methyltetrahydropyranYield 41.1%

Procedure

Using the procedure described in the portion of Example 1 which is concerned with the preparation of starting materials, a Grignard reagent was prepared from 3-benzyloxybromobenzene (10.5 g) and 2-methyltetrahydropyran-4-one (2.28 g) was added. The mixture was stirred at ambient temperature for 3 hours, acidified by the addition of 2N hydrochloric acid solution and extracted with ethyl acetate. Column chromatography, using a 10:3 v/v mixture of toluene and ethyl acetate as eluent, gave a less polar isomer, (2RS,4SR)-4-(3-benzyloxyphenyl)-4-hydroxy-2-methyltetrahydropyran (2.45 g, 41%), as an oil,

Workup

  1. customis concerned with the preparation of starting materials
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. additiona 10:3 v/v mixture of toluene and ethyl acetate as eluent

Sources & evidence

ORD record
ord-3b6b3507a0fc464c891583dc53def1ee
Source dataset
uspto-grants-1992_03
Patent number
US05098930

Reaction notes

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