4-Toluenesulfonyl chloride → (RS)-Toluene-4-sulfonic acid 6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl ester

HRID 278458Notes

Reaction equation

HRID 278458 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][OH:14])[CH2:7][CH2:6]2.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][O:14][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10058404(6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol

Product 1

HCID 11405260(RS)-Toluene-4-sulfonic acid 6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(RS)-(6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-methanol (939 mg, 4.88 mmol), p-toluenesulfonyl chloride (934 mg, 4.9 mmol), triethylamine (1.12 ml, 7.88 mmol) and N,N-dimethyl aminopyridine (10 mg) in CH2Cl2 (10 ml) was stirred together at ambient temperature for 24 hr. Acidification with 1N HCl (pH 1-2), extraction of the aqueous phase with CH2Cl2 (2×20 ml), drying (Na2SO4) filtration and evaporation afforded the crude product which wag chomatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc-n-Hexane (1:3) to afford the title compound as a colourless oil (1.37 g, 3.95 mmol, 81%), MS m/e=346.1 (M+).

Workup

  1. extractionAcidification with 1N HCl (pH 1-2), extraction of the aqueous phase with CH2Cl2 (2×20 ml)
  2. customdrying
  3. filtration(Na2SO4) filtration and evaporation
  4. customafforded the crude product which wag
  5. washeluting with EtOAc-n-Hexane (1:3)

Sources & evidence

ORD record
ord-4f147cb4a201456a8db3f8a16aca8e5c
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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