4-Toluenesulfonyl chloride → (+/-)-2,3,6,7,8,9-Hexahydronaphtho[1,2-b]furan-2-ylmethyl 4-methylbenzenesulfonate

HRID 13922Notes

Reaction equation

HRID 13922 reaction equation
[O:1]1[CH:5]([CH2:6][OH:7])[CH2:4][C:3]2[CH:8]=[CH:9][C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=3[C:2]1=2.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1.O>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:7][CH2:6][CH:5]2[O:1][C:2]3[C:15]4[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=4[CH:9]=[CH:8][C:3]=3[CH2:4]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 68583650(+/-)-2,3,6,7,8,9-Hexahydronaphtho[1,2-b]furan-2-ylmethanol

Product 1

HCID 86598543(+/-)-2,3,6,7,8,9-Hexahydronaphtho[1,2-b]furan-2-ylmethyl 4-methylbenzenesulfonateYield 85.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (±)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethanol (1.37 g, 6.71 mmol) in dichloromethane (50 mL) was added p-toluenesulfonyl chloride (2.56 g, 13.41 mmol), 4-(dimethylamino)pyridine (0.164 g, 1.34 mmol), and triethylamine (1.70 g, 16.77 mmol) and the reaction mixture was allowed to stir at 40° C. for 12 h. The reaction mixture was diluted with water (250 mL) and the aqueous layer extracted with dichloromethane (2×150 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, dried (magnesium sulfate), and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:5) gave 2.05 g (85%) of (±)-2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethyl 4-methylbenzenesulfonate as a colorless oil. Rf=0.5 (silica, ethyl acetate:hexanes 1:4); Anal. calcd. for C20H22O4S: C, 67.01; H, 6.19. Found: C, 66.50; H, 6.27.

Workup

  1. extractionthe aqueous layer extracted with dichloromethane (2×150 mL)
  2. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. customthe solvent was removed in vacuo
  5. customto provide a crude oil
  6. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:5)

Sources & evidence

ORD record
ord-b472fbfb0d50485bb30aade7a56f6e38
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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