Sodium Bicarbonate → HCID 59201065, compound

HRID 1690153Notes

Reaction equation

HRID 1690153 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]([C:12]1[CH:27]=[CH:26][C:15]([O:16][C:17]2[CH:18]=[C:19]([CH:23]3[CH2:25][O:24]3)[CH:20]=[CH:21][CH:22]=2)=[C:14]([CH2:28][CH2:29][CH3:30])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1>[F:1][C:2]([F:31])([F:32])[C:3]([C:12]1[CH:27]=[CH:26][C:15]([O:16][C:17]2[CH:18]=[C:19]([CH2:23][CH2:25][OH:24])[CH:20]=[CH:21][CH:22]=2)=[C:14]([CH2:28][CH2:29][CH3:30])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:5])([F:7])[F:6]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 59201144HCID 59201144, compound

Product 1

HCID 59201065HCID 59201065, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)phenyl) oxirane (550 mg, 1.18 mmol) in tetrahydrofuran (10 mL), boron trifluoride diethyl ether complex (400 μl) and sodium cyanoborohydride (222 mg) were added at 0° C. under an argon atmosphere, and the resultant mixture was stirred. After completion of the reaction, the reaction solution was added with a saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate, and then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (252 mg, yield 46%) was obtained as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-05e7d9b051a642eb8cb7b7fd516f2e69
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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