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Acetonitrile → 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-(4-(3-(2-(4,4,5,5,5-pentafluoropentylthio)ethoxy)-(R)-2-hydroxypropyloxy)phenyl)chroman

HRID 1792359
Notes
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Reaction equation

HRID 1792359 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[C:10]([CH3:25])([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][O:23][CH3:24])=[CH:17][CH:16]=3)[CH2:11][O:12]2)=[CH:7][CH:6]=1.[O:33]1[CH2:35][CH:34]1[CH2:36][O:37][CH2:38][CH2:39][S:40][CH2:41][CH2:42][CH2:43][C:44]([F:50])([F:49])[C:45]([F:48])([F:47])[F:46].C(#N)C>N1C=CC=CC=1.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([C:26]3[CH:27]=[CH:28][C:29]([O:32][CH2:35][C@H:34]([OH:33])[CH2:36][O:37][CH2:38][CH2:39][S:40][CH2:41][CH2:42][CH2:43][C:44]([F:50])([F:49])[C:45]([F:46])([F:47])[F:48])=[CH:30][CH:31]=3)[C:10]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][O:23][CH3:24])=[CH:19][CH:20]=3)([CH3:25])[CH2:11][O:12]2)=[CH:7][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 22033218(3RS,4RS)-7-methoxymethoxy-3-methyl-3-(4-methoxymethoxyphenyl)-4-(4-hydroxyphenyl)chromanHCID 220332271-((2-Oxiranyl)methoxy)-2-(4,4,5,5,5-pentafluoropentylthio)ethane

Product 1

HCID 205992647-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-(4-(3-(2-(4,4,5,5,5-pentafluoropentylthio)ethoxy)-(R)-2-hydroxypropyloxy)phenyl)chromanYield 86.3%

Reagents, catalysts & solvents

2
HCID 1049PyridineCatalystHCID 962WaterSolvent2×

Procedure

A mixture of (3RS,4RS)-7-methoxymethoxy-3-methyl-3-(4-methoxymethoxyphenyl)-4-(4-hydroxyphenyl)chroman (31 1 mg, 0.71 mmole), 1-((2-oxiranyl)methoxy)-2-(4,4,5,5,5-pentafluoropentylthio)ethane (568 mg, 1.93 mmole), acetonitrile (9 ml), water (3 ml) and pyridine (5 drops) was refluxed for 10 hours. After cooling, the reaction mixture was diluted with water and the aqueous phase was extracted with ethyl acetate. Then, the organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=3:1) to give the title compound (448 mg, yield 86%) as a colorless oil.

Workup

  1. temperaturewas refluxed for 10 hours
  2. temperatureAfter cooling
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThen, the organic layer was washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cc4b6fb557c949cdacf059adb68c10e0
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074819B2

Reaction notes

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