3,4-dihydro-2H-pyran → 4-Tetrahydropyranyloxy-4,5,6,7-tetrahydrobenzo[b]thiophene

HRID 653445Notes

Reaction equation

HRID 653445 reaction equation
[OH:1][CH:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1>C(Cl)Cl>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:1][CH:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 139116314-Hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophene

Product 1

HCID 139116324-Tetrahydropyranyloxy-4,5,6,7-tetrahydrobenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 19.0 g (0.123 mol) of product from Step A, 15.53 g (0.185 mol) of dihydropyran, 2.56 g (0.010 mol) of pyridinium-4-toluenesulfonate, and 700 ml CH2Cl2 was stirred at ambient temperature for 5 hours. The reaction mixture was washed twice with half saturated NaCl solution, dried (Na2SO4), filtered, and evaporated. The residual colorless oil was distilled (112° C., 0.05 mm Hg) yielding a quantitative amount of product.

Workup

  1. washThe reaction mixture was washed twice with half saturated NaCl solution
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. distillationThe residual colorless oil was distilled (112° C., 0.05 mm Hg)
  6. customyielding a quantitative amount of product

Sources & evidence

ORD record
ord-c61e67cebbdb4b9eb5b835ece90927b8
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

Loading…