(+/-)-Dimethyl (3-methyl-2-oxo-6-phenylhex-5-yn-1-yl)phosphonate → (+/-)-Dimethyl (3-methyl-2-oxo-6-phenylhexyl)phosphonate

HRID 59689Notes

Reaction equation

HRID 59689 reaction equation
[CH3:1][CH:2]([CH2:12][C:13]#[C:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3](=[O:11])[CH2:4][P:5](=[O:10])([O:8][CH3:9])[O:6][CH3:7]>[Pd].CO>[CH3:1][CH:2]([CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:3](=[O:11])[CH2:4][P:5](=[O:10])([O:8][CH3:9])[O:6][CH3:7]

Participants

4

Reactant 1

HCID 90054514(+/-)-Dimethyl (3-methyl-2-oxo-6-phenylhex-5-yn-1-yl)phosphonate

Product 1

HCID 90054530(+/-)-Dimethyl (3-methyl-2-oxo-6-phenylhexyl)phosphonateYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture consisting of (±)-dimethyl (3-methyl-2-oxo-6-phenylhex-5-yn-1-yl)phosphonate (15db(i)/15dc(i)), (1.0 g, 3.4 mmol) and 10% palladium on activated carbon (15 mg) in methanol (30 mL) was stirred under an atmosphere of hydrogen overnight. The hydrogen was evacuated and the mixture was filtered through a micropore filter. The filtrate was concentrated in vacuo to afford the title compound (1.0 g, quantitative yield) as a clear oil; 1H-NMR (CDCl3) δ 7.3-7.25 (m, 2H), 7.2-7.1 (m, 3H), 3.8-3.7 (m, 6H), 3.1 (d, 2H), 2.8-2.75 (m, 1H), 2.7-2.5 (m, 2H), 1.8-1.65 (m, 1H), 1.65-1.5 (m, 2H), 1.4-1.3 (m, 1H), 1.1 (d, 3H); MS (ESI−) m/z 299 (M+1).

Workup

  1. customThe hydrogen was evacuated
  2. filtrationthe mixture was filtered through a micropore
  3. filtrationfilter
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-566ada7c9f5f4f68b2d98f4db8694273
Source dataset
uspto-grants-2016_09
Patent number
US09440919B2

Reaction notes

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