Water → HCID 22123580, compound

HRID 1859298Notes

Reaction equation

HRID 1859298 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[C:15]2[CH:16]=[CH:17][C:18]([O:20][CH2:21][O:22][CH3:23])=[CH:19][C:14]=2[O:13][CH2:12][C:11]1([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][O:33][CH3:34])=[CH:27][CH:26]=1)[CH3:24].ClCCl.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1.O>N1C=CC=CC=1>[CH3:23][O:22][CH2:21][O:20][C:18]1[CH:17]=[CH:16][C:15]2[CH:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][S:44]([C:41]3[CH:42]=[CH:43][C:38]([CH3:48])=[CH:39][CH:40]=3)(=[O:46])=[O:45])[C:11]([C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][O:33][CH3:34])=[CH:29][CH:30]=3)([CH3:24])[CH2:12][O:13][C:14]=2[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 22033247HCID 22033247, compound

Product 1

HCID 22123580HCID 22123580, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(3RS,4RS)-4-(8-Hydroxyoctyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran (80 mg, 0.17 mmol) was dissolved in pyridine (2 ml) and dichloromethane (0.5 ml) and then cooled to 0° C. p-Toluenesulfonylchloride (0.12 g, 0.63 mmol) was added thereto and the mixture was stirred for 6 hours at room temperature. Water was added thereto at 0° C. and the reaction solution was extracted with ethyl acetate, washed with saturated saline and then dried over magnesium sulfate. The residue was subjected to column chromatography (n-hexane:ethyl acetate=4:1) to obtain 110 mg (yield: ~100%) of the title compound as a colorless oil.

Workup

  1. additionwas added
  2. extractionat 0° C. and the reaction solution was extracted with ethyl acetate
  3. washwashed with saturated saline
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-1ad12794840f42abbb6ce03d87c8e2c5
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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