4-Toluenesulfonyl chloride → 1,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl p-toluenesulfonate

HRID 364756Notes

Reaction equation

HRID 364756 reaction equation
[CH3:1][O:2][C:3]([O:19][CH3:20])([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1)[CH:4]([OH:6])[CH3:5].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(N(CC)CC)C>[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O:6][CH:4]([CH3:5])[C:3]([O:19][CH3:20])([O:2][CH3:1])[C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=3)[CH:8]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 113003471,1-Dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol

Product 1

HCID 200291641,1-Dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1,1-dimethoxy-1-(6-methoxy-2-naphthyl)propan-2-ol is treated with a molar excess of p-toluenesulfonyl chloride in the presence of a molar excess of triethylamine in a manner similar to Example 25 to yield (S) 1,1-dimethoxy-1-(6-methoxy-2-naphthyl)prop-2-yl p-toluenesulfonate. That material is converted to (S) methyl 2-(6-methoxy-2-naphthyl)propionate in a manner similar to that described in Example 17.

Sources & evidence

ORD record
ord-582dca22265b44f594bc493f5d620cbb
Source dataset
uspto-grants-1986_08
Patent number
US04605758

Reaction notes

Loading…