Sodium hydride → HCID 86758625, compound

HRID 2296728Notes

Reaction equation

HRID 2296728 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CN(C=O)C>[C:10]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][O:9][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74662beta-Phenylphenethyl alcoholHCID 79177tert-Butyl bromoacetate

Product 1

HCID 86758625HCID 86758625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2,2-diphenylethanol (1 g) in DMF (10 mL) was added 60% sodium hydride (350 mg) at 0° C. under Ar. The solution was stirred for 10 min, and t-butyl bromoacetate (888 uL) was added, and the solution was warmed to RT. After stirring 30 min, the reaction was quenched with water (20 mL), and the aqueous solution was extracted with ether (25 mL). The organic layer was washed with water (20 mL) and brine (20 mL). The organic solution was dried (MgSO4), and silica gel flash chromatography (3% ethyl acetate/hexanes) yielded t-butyl (2,2-diphenylethoxy)acetate. The intermediate was treated with 25% TFA/CH2Cl2 for 1 h. The solvent was removed, and traces of TFA was removed by azeotroping with toluene to yield the title compound. 1H NMR (CDCl3) δ 7.1-7.4 (m, 10H), 4.32 (t, J=8.4 Hz, 1H), 4.0-4.1 (m, 4H).

Workup

  1. stirringAfter stirring 30 min
  2. customthe reaction was quenched with water (20 mL)
  3. extractionthe aqueous solution was extracted with ether (25 mL)
  4. washThe organic layer was washed with water (20 mL) and brine (20 mL)
  5. dry with materialThe organic solution was dried (MgSO4), and silica gel flash chromatography (3% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-be7361fd2a0949e4ae9c4e763901c212
Source dataset
uspto-grants-2002_12
Patent number
US06489339B1

Reaction notes

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