p-Toluenesulfonic acid → HCID 86739366, compound

HRID 637529Notes

Reaction equation

HRID 637529 reaction equation
[Br:1][C:2]([C@H:5]1[C@H:9]([OH:10])[O:8][C:7](=[O:11])[CH2:6]1)([CH3:4])[CH3:3].[CH3:12][C@H:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:15]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Br:1][C:2]([C@H:5]1[C@H:9]([O:10][CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:15]=2)[CH3:12])[O:8][C:7](=[O:11])[CH2:6]1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12882420HCID 12882420, compoundHCID 86739367HCID 86739367, compound

Product 1

HCID 86739366HCID 86739366, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 6.07 g of dl trans 4-(2-bromo-prop-2-yl)-5-hydroxy-tetrahyrofuran-2-one, 5.83 of (S)α-methyl-3-phenoxy-benzyl alcohol, 300 mg of p-toluene sulfonic acid, 60 ml of benzene and 10 g of colored Actigel deshydratant was stirred at 20°-25° C. for 24 hours and the reaction mixture was washed with aqueous sodium bicarbonate solution. The mixture was extracted with benzene and the organic phase was dried and evaporated to dryness under reduced pressure to obtain 9.5 g of residue. The residue was chromatographed over silica gel and was eluted with methylene chloride to obtain 5 g of A and B isomers of trans 4-(2-bromo-propy-2-yl)-5-[(3-phenoxyphenyl)-methyl-methoxy]-tetrahydrofuran-2-one. Crystallization from isopropyl ether containing 30% of petroleum ether yielded 960 mg of the B isomer melting at ≃76° C. and having a specific rotation of [α]D20 =+188.5° (c=1% in benzene). Chromatography of the mother liquors over silica gel and elution with methylene chloride obtained the A isomer in the form of an oil.

Workup

  1. washthe reaction mixture was washed with aqueous sodium bicarbonate solution
  2. extractionThe mixture was extracted with benzene
  3. customthe organic phase was dried
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-65000dbb507c4573b568a2f25b8f408d
Source dataset
uspto-grants-1985_12
Patent number
US04556732

Reaction notes

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