Water → HCID 86639417, compound

HRID 1690183Notes

Reaction equation

HRID 1690183 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[C:16]([CH2:17][CH2:18][CH3:19])=[CH:15][C:14]([C:20]([O:29][CH2:30][O:31][CH3:32])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:13][C:12]=2[CH2:33][CH2:34][CH3:35])=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+].O>CO>[I:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[C:16]([CH2:17][CH2:18][CH3:19])=[CH:15][C:14]([C:20]([O:29][CH2:30][O:31][CH3:32])([C:21]([F:22])([F:23])[F:24])[C:25]([F:27])([F:28])[F:26])=[CH:13][C:12]=2[CH2:33][CH2:34][CH3:35])=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86639415HCID 86639415, compound

Product 1

HCID 86639417HCID 86639417, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2-iodo-5-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2,6-dipropylphenoxy) benzaldehyde (25 mg, 0.0404 mmol) in methanol (2.0 mL), sodium borohydride (1.7 mg, 0.445 mmol) was added under ice-cold conditions, and the resultant mixture was stirred for 30 minutes. After completion of the reaction, the reaction solution was added with water under ice-cold conditions and extracted with chloroform. The organic layer was washed with brine and dried over sodium sulfate. (2-Iodo-5-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2,6-dipropylphenoxy) phenyl)methanol (27 mg, yield >100%) was obtained as a yellow oil.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-c851dbd088c94742ba288a872042344c
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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