Methanesulfonyl chloride → HCID 131714021, compound

HRID 1153907Notes

Reaction equation

HRID 1153907 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[C:25]([O:28][C:29]1([CH2:53][CH2:54][CH2:55][OH:56])[CH2:34][C:33]2[CH:35]=[CH:36][C:37]([O:39][CH:40]([CH2:42][CH2:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH3:41])=[CH:38][C:32]=2[O:31][C:30]1([CH3:52])[CH3:51])(=[O:27])[CH3:26].[CH3:57][S:58](Cl)(=[O:60])=[O:59]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[C:25]([O:28][C:29]1([CH2:53][CH2:54][CH2:55][O:56][S:58]([CH3:57])(=[O:60])=[O:59])[CH2:34][C:33]2[CH:35]=[CH:36][C:37]([O:39][CH:40]([CH2:42][CH2:43][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH3:41])=[CH:38][C:32]=2[O:31][C:30]1([CH3:51])[CH3:52])(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 131714017HCID 131714017, compound

Product 1

HCID 131714021HCID 131714021, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

To 1.823 g (4.15 mmole) dl-5-acetoxy-3-(3-hydroxypropyl)-2,2-dimethyl-7-(5-phenyl-2-pentyloxy)-3,4-dihydro-2H-benzopyran was added 20 ml of pyridine, the mixture stirred under nitrogen to affect solution and cooled to 5° C. Methanesulfonyl chloride, 520 mg (4.56 mmole), was added, the resulting mixture stirred at 5°-10° C. for 20 minutes, then allowed to warm to room temperature and stirred for an additional 50 minutes. The mixture was concentrated in vacuo and the residual oil taken up in ethyl acetate, washed twice with water, once with brine and the organic layer dried over anhydrous magnesium sulfate. After evaporation of solvent in vacuo the desired product was obtained as an oil, 1.999 g.

Workup

  1. stirringthe resulting mixture stirred at 5°-10° C. for 20 minutes
  2. temperatureto warm to room temperature
  3. stirringstirred for an additional 50 minutes
  4. concentrationThe mixture was concentrated in vacuo
  5. washwashed twice with water, once with brine
  6. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  7. customAfter evaporation of solvent in vacuo the desired product
  8. customwas obtained as an oil, 1.999 g

Sources & evidence

ORD record
ord-3faaafda81024a8a8ac19b7dd1c8c2b0
Source dataset
uspto-grants-1984_12
Patent number
US04486428

Reaction notes

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