Water → HCID 54378120, compound

HRID 278447Notes

Reaction equation

HRID 278447 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH2:7][CH:8]([CH2:10][OH:11])[O:9][C:5]=2[CH:4]=1.CCN(CC)CC.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH2:7][CH:8]([CH2:10][O:11][S:27]([C:24]3[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=3)(=[O:29])=[O:28])[O:9][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 22628398(6-Methoxy-2,3-dihydro-1-benzofuran-2-yl)methanol

Product 1

HCID 54378120HCID 54378120, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (RS)-(6-methoxy-2,3-dihydro-benzofuran-2-yl)-methanol (0.09 g, 0.5 mmol), Et3N (0.1 ml, 0.75 mmol), DMAP (1 mg, 0.01 mmol) in CH2Cl2 (1.5 ml) at 0° C. was added dropwise a solution of p—toluenesulfonylchloride (115 mg, 0.6 mmol). The reaction mixture was allowed to warm to room temperature and was stirred during 4 hr before the addition of H2O (2 ml). The aqueous phase was extracted with CH2Cl2 (2×5 ml). Combined organic phases were dried over Na2SO4, and concentrated. The residue was chromatographed over SiO2 (Merck 230-400 mesh) eluting with nHexane-EtOAc (4:1) to provide (RS)-toluene-4-sulfonic acid 6-methoxy-2,3-dihydro-benzofuran-2-ylmethyl ester (120 mg, 72%) as a colorless oil, MS:m/e=334 (M+).

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2 (2×5 ml)
  2. dry with materialCombined organic phases were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed over SiO2 (Merck 230-400 mesh)
  5. washeluting with nHexane-EtOAc (4:1)

Sources & evidence

ORD record
ord-f7d1b9c78bd14cf5b0d86e1f3be3f33c
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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