p-Toluenesulfonic acid → HCID 69053929, compound

HRID 1727230Notes

Reaction equation

HRID 1727230 reaction equation
[C:1]([O:4][C@@H:5]1[C:14]([CH3:15])=[CH:13][C@H:12]2[C@@:7]([OH:20])([C@@H:8]([CH3:19])[CH2:9][CH2:10][C@H:11]2[C:16]([CH3:18])=[CH2:17])[C@H:6]1[OH:21])(=[O:3])[CH3:2].[C:22]1(C)[CH:27]=CC(S(O)(=O)=O)=C[CH:23]=1>COC(OC)(C)C>[C:1]([O:4][C@H:5]1[C@@H:6]2[O:21][C:22]([CH3:27])([CH3:23])[O:20][C@:7]32[C@@H:12]([C@H:11]([C:16]([CH3:18])=[CH2:17])[CH2:10][CH2:9][C@@H:8]3[CH3:19])[CH:13]=[C:14]1[CH3:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 69056915HCID 69056915, compound

Product 1

HCID 69053929HCID 69053929, compoundYield 776%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Procedure

A stirred solution of (1S,2R,4aR,5R,8S,8aS)-1,8a-dihydroxy-5-isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-2-naphthalenyl acetate (Preparation 126, 10 g) in 2,2-dimethoxypropane (200 ml) was treated with para-toluenesulfonic acid (700 mg). After 3 days, the solution was concentrated in vacuo and the residue purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (5:95) to give the product (10.55 g).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customthe residue purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane (5:95)

Sources & evidence

ORD record
ord-f1673abc16654821aa09436145d386fd
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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