Dichloromethane → 9-{7-(Methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methylchroman-4-yl}nonyl 4-methylbenzenesulfonate

HRID 1859294Notes

Reaction equation

HRID 1859294 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[C:16]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][O:23][CH3:24])=[CH:20][C:15]=2[O:14][CH2:13][C:12]1([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=1)[CH3:25].ClCCl.[C:39]1([CH3:49])[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1>N1C=CC=CC=1>[CH3:24][O:23][CH2:22][O:21][C:19]1[CH:18]=[CH:17][C:16]2[CH:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:1][S:45]([C:42]3[CH:43]=[CH:44][C:39]([CH3:49])=[CH:40][CH:41]=3)(=[O:47])=[O:46])[C:12]([C:26]3[CH:27]=[CH:28][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:30][CH:31]=3)([CH3:25])[CH2:13][O:14][C:15]=2[CH:20]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 154817594-(9-Hydroxynonyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

Product 1

HCID 154817609-{7-(Methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methylchroman-4-yl}nonyl 4-methylbenzenesulfonateYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(3RS,4RS)-4-(9-Hydroxynonyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran (90 mg, 0.19 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 dropwise thereto, and the mixture was stirred for 3 hours at room temperature, quenched with water and then extracted with ethyl acetate. The extracted organic substance was washed with 2N hydrochloric acid, dried over magnesium sulfate and then concentrated. The residue was subjected to column chromatography (n-hexane:ethyl acetate=4:1) to obtain 105 mg (yield: 88%) of the title compound as a colorless oil.

Workup

  1. additionwas added dropwise
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extracted organic substance was washed with 2N hydrochloric acid
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9385de1d8c384493867ab5067ab2a385
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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