p-Toluenesulfonic acid → HCID 57810030, compound

HRID 2106039Notes

Reaction equation

HRID 2106039 reaction equation
CC1(C)[O:6][C:5]([CH2:11][C:12]([C:15]2[C:23]3[O:22][CH2:21][CH2:20][C:19]=3[CH:18]=[C:17]([S:24][CH3:25])[CH:16]=2)([CH3:14])[CH3:13])([C:7]([F:10])([F:9])[F:8])[CH2:4][O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:14][C:12]([C:15]1[C:23]2[O:22][CH2:21][CH2:20][C:19]=2[CH:18]=[C:17]([S:24][CH3:25])[CH:16]=1)([CH3:13])[CH2:11][C:5]([C:7]([F:8])([F:9])[F:10])([OH:6])[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 69063435HCID 69063435, compound

Product 1

HCID 57810030HCID 57810030, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.31 g of 7-[2-(2,2-dimethyl-4-trifluoromethyl-[1,3]dioxolan-4-yl)-1,1-dimethylethyl]-5-methylsulfanyl-2,3-dihydrobenzofuran and 0.015 g of p-toluenesulfonic acid (p-TsOH) monohydrate in methanol (10 mL) was stirred at room temperature for 7 days, heated to reflux for 1 minute, and the volatiles removed in vacuo. The residue was diluted with saturated aqueous sodium bicarbonate and filtered. The solid was washed with water and hexanes, and dried to give 0.235 g of 4-methyl-4-(5-methylsulfanyl-2,3-dihydrobenzofuran-7-yl)-2-trifluoromethylpentane-1,2-diol.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 minute
  3. customthe volatiles removed in vacuo
  4. additionThe residue was diluted with saturated aqueous sodium bicarbonate
  5. filtrationfiltered
  6. washThe solid was washed with water and hexanes
  7. customdried

Sources & evidence

ORD record
ord-a5d71a72c6fe4edc836648a6ad1d5f50
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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