Methanol → HCID 22123615, compound

HRID 1859323Notes

Reaction equation

HRID 1859323 reaction equation
[OH:1][C:2]1[CH:41]=[CH:40][C:5]2[CH:6]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29][CH2:30][CH2:31][CH2:32][C:33]([F:39])([F:38])[C:34]([F:37])([F:36])[F:35])[CH:19]=3)[C:7]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)([CH3:10])[CH2:8][O:9][C:4]=2[CH:3]=1.C[OH:43]>O>[OH:1][C:2]1[CH:41]=[CH:40][C:5]2[CH:6]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29]([CH2:30][CH2:31][CH2:32][C:33]([F:39])([F:38])[C:34]([F:35])([F:36])[F:37])=[O:43])[CH:19]=3)[C:7]([C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)([CH3:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 22123600HCID 22123600, compound

Product 1

HCID 22123615HCID 22123615, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(3RS,4RS)-7-Hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[3-(4-(4,4,5,5,5-pentafluoropentylthio)butyloxy)phenyl]-2,3-dihydro-4H-benzopyran (72 mg, 0.12 mmol) was dissolved in methanol (5 ml) and water (1 ml), and NaIO4 (35 mg, 0.16 mmol) was added thereto. The reaction solution was stirred for 12 hours at room temperature and then extracted with ethyl acetate. The organic layer thus separated was washed with water, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to column chromatography (n-hexane:ethyl acetate=2:1) to obtain 66 mg (yield: 89%) of the title compound as a white foam.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer thus separated
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-99db2a4e9bac4d51825710e7a5457d82
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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