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Methanol → (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]thiochroman

HRID 1859317
Notes
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Reaction equation

HRID 1859317 reaction equation
C[OH:2].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][S:31][CH2:32][CH2:33][CH2:34][C:35]([F:41])([F:40])[C:36]([F:39])([F:38])[F:37])[C:9]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)([CH3:14])[CH2:10][S:11]2)=[CH:6][CH:5]=1>O>[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][S:31]([CH2:32][CH2:33][CH2:34][C:35]([F:41])([F:40])[C:36]([F:37])([F:38])[F:39])=[O:2])[C:9]([C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)([CH3:14])[CH2:10][S:11]2)=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 887MethanolHCID 22033340(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]thiochroman

Product 1

HCID 22033383(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]thiochromanYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methanol (16 ml) and water (4 ml) were added to the mixture of (3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]thiochroman (85 mg, 0.14 mmol) obtained in Example 33 and NaIO4 (34 mg, 0.16 mmol), and the reaction mixture was stirred for 3.5 hours at room temperature. Water was added to the reaction solution which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then purified with preparative TLC (n-hexane:ethyl acetate=1:1) to obtain 39 mg (yield: 45%) of the title compound as a white solid. In this reaction, 13 mg (15%) of the unreacted starting 3RS,4RS-compound was recovered.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. custompurified with preparative TLC (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ba1b112b94114af5964ce106050d94f3
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06153768

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes