Methanol → HCID 9829958, compound

HRID 1859296Notes

Reaction equation

HRID 1859296 reaction equation
[OH:1][C:2]1[CH:39]=[CH:38][C:5]2[CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][S:27][CH2:28][CH2:29][CH2:30][C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[F:33])[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:41].O>O1CCOCC1>[OH:1][C:2]1[CH:39]=[CH:38][C:5]2[CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][S:27]([CH2:28][CH2:29][CH2:30][C:31]([F:37])([F:36])[C:32]([F:33])([F:34])[F:35])=[O:41])[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

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 15481762HCID 15481762, compound

Product 1

HCID 9829958HCID 9829958, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(3RS,4RS)-7-Hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]-2,3-dihydro-4H-benzopyran (47 mg, 0.08 mmol) was dissolved in 1,4-dioxane (1 ml), methanol (1 ml) and water (0.25 ml). NaIO4 (20 mg, 0.093 mmol) was added dropwise thereto, and the reaction mixture was stirred for 12 hours at room temperature and then filtered. The filtrate was concentrated and the residue was subjected to column chromatography (n-hexane:ethyl acetate=3:1→1:1) to obtain 35 mg (yield: 73%) of the title compound as a colorless oil.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7f4f52e021b64b40b08a2db76fb518ac
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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