Water → HCID 58494111, compound

HRID 1942693Notes

Reaction equation

HRID 1942693 reaction equation
C([O:3][C:4](=O)[CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[C:12]=1[CH2:18][CH3:19])[C:6](OCC)=[O:7])C.[BH4-].[Na+].O>CO>[Br:17][C:13]1[C:12]([CH2:18][CH3:19])=[C:11]([CH:5]([CH2:6][OH:7])[CH2:4][OH:3])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58494029HCID 58494029, compound

Product 1

HCID 58494111HCID 58494111, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(3-bromo-2-ethyl-phenyl)-malonic acid diethyl ester (D127) (13 g, 37.88 mmol) in methanol (130 mL) was added sodium borohydride (14.33 g, 378.78 mmol), the reaction mixture was stirred for 12 hr at room temperature. Then water was added and extracted with CH2Cl2. The organic layers were separated, dried over Na2SO4, and concentrated in vacuo to afford 2-(3-bromo-2-ethyl-phenyl)-propane-1,3-diol (D128) (8 g). MS (ES): C11H15BrO2 requires 258.0. found 223.0 (M+H+-36).

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic layers were separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be15f331e1cd4401b3c7f9b73c71c31a
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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