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

HRID 1516112Notes

Reaction equation

HRID 1516112 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-butyldimethysilyloxy-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, 0.94 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-986d705eb6054513a7fc1463583fe451
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

Loading…