Phenylacetaldehyde → HCID 68828540, compound

HRID 1453966Notes

Reaction equation

HRID 1453966 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8]=O)=[CH:3][CH:2]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:18]23[CH2:27][CH2:26][CH2:25][CH2:24][C:23]2([CH3:28])[CH2:22][NH:21][CH2:20][CH2:19]3)[CH:15]=[CH:16][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:8]([N:21]1[CH2:20][CH2:19][C:18]2([C:14]3[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH3:10])[CH:13]=3)[C:23]([CH3:28])([CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:22]1)[CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 998PhenylacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68828269HCID 68828269, compound

Product 1

HCID 68828540HCID 68828540, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Phenacetaldehyde 87 mg (0.72 mmol) and 190 mg (0.72 mmol) of 10 were mixed in 1,2-dichloroethane (15 mL) and then treated with sodium triacetoxyborohydride 230 mg (1.08 mmol). The reaction mixture remained cloudy throughout the reaction. The mixture was stirred at room temperature under N2 atmosphere for 2 h. The reaction mixture was quenched by adding saturated NaHCO3, and the product was extracted with EtOAc. The EtOAc extract was dried (MgSO4), and the solvent was evaporated to give 0.25 g (95%) of a light yellow oil. Purification by chromatography on alumina using 10% ethyl acetate/hexane gave 0.23 g (89%) of desired product 11 as colorless clear viscous oil: 13C NMR (300 MHz, CDCl3) δ 158.9, 129.1, 128.6, 128.1, 126.2, 122.5, 117.1, 109.9, 63.2, 61.1, 55.5, 43.1, 37.4, 36.3, 34.0, 30.7, 22.4, 22.1.

Workup

  1. customThe reaction mixture remained cloudy throughout the reaction
  2. customThe reaction mixture was quenched
  3. additionby adding saturated NaHCO3
  4. extractionthe product was extracted with EtOAc
  5. extractionThe EtOAc extract
  6. dry with materialwas dried (MgSO4)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ac52bb837dca42d9aeeb812c194a4f6c
Source dataset
uspto-grants-2009_01
Patent number
US07476679B2

Reaction notes

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