Methanol → HCID 22123622, compound

HRID 1859332Notes

Reaction equation

HRID 1859332 reaction equation
[OH:1][C:2]1[CH:41]=[CH:40][C:5]2[CH:6]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][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:18]=3)[CH:7]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)[CH2:8][O:9][C:4]=2[CH:3]=1.C[OH:43].O>O1CCOCC1>[OH:1][C:2]1[CH:41]=[CH:40][C:5]2[CH:6]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][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:18]=3)[CH:7]([C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 22123598HCID 22123598, compound

Product 1

HCID 22123622HCID 22123622, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

7-Hydroxy-3-(4-hydroxyphenyl)-4-[3-(5-(4,4,5,5,5-pentafluoropentylthio)pentyloxy)phenyl]-2,3-dihydro-4H-benzopyran (90 mg, 0.15 mmol) was dissolved in 1,4-dioxane (1.5 ml), methanol (1.5 ml) and water (0.38 ml), and NaIO4 (35.5 mg, 0.16 mmol) was added dropwise thereto. The reaction solution was stirred for 8 hours at room temperature and then filtered. The filtrate was concentrated and the residue was separated by column chromatography (n-hexane:ethyl acetate=1:1) to obtain 58 mg (yield: 63%, 3RS,4RS/3RS,4SR=1:1) of the title compound as a colorless oil.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residue was separated by column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-84c9eedd7a4b4a079ace4b658d0d62bc
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

Loading…