2-Methylbenzenesulfonic acid → 1-Tert-butyldimethylsilyloxy-2-tetrahydropyranyloxy-2-(4-tertbutylphenyl) ethane

HRID 1392886Notes

Reaction equation

HRID 1392886 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([OH:21])[C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C1(C)C(S(O)(=O)=O)=CC=CC=1>ClCCl>[Si:1]([O:8][CH2:9][CH:10]([O:21][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][O:22]1)[C:11]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 596786511-Tert-butyldimethylsilyloxy-2-hydroxy-2-(4-tert-butylphenyl)ethane

Product 1

HCID 596786401-Tert-butyldimethylsilyloxy-2-tetrahydropyranyloxy-2-(4-tertbutylphenyl) ethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Tert-butyldimethylsilyloxy-2-hydroxy-2-(4-tert-butylphenyl) ethane (0.5 g, 1.622 mmol) is dissolved in dichloromethane and to it is added dihydropyran (0.163 g,1.94 mmol) and toluenesulfonic acid (33 mg, 0.194 mmol). The reaction is stirred for 2 hours after which the mixture is washed with water and dried. The crude residue obtained after concentration is purified by flash chromatography (silica gel; ethyl acetate/hexanes) to obtain the product.

Workup

  1. washis washed with water
  2. customdried

Sources & evidence

ORD record
ord-dedfcd3ea4d342b492f59cf3ce706144
Source dataset
uspto-grants-2008_03
Patent number
US07344702B2

Reaction notes

Loading…