Ethyl diethoxymethyl(benzyl)phosphinate → Ethyl diethoxymethyl(cyclohexylmethyl)phosphinate

HRID 973649Notes

Reaction equation

HRID 973649 reaction equation
[CH2:1]([O:3][CH:4]([P:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:12])[O:9][CH2:10][CH3:11])[O:5][CH2:6][CH3:7])[CH3:2]>C(O)C.[Ni]>[CH2:1]([O:3][CH:4]([P:8]([CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)(=[O:12])[O:9][CH2:10][CH3:11])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

4

Reactant 1

HCID 9994134Ethyl diethoxymethyl(benzyl)phosphinate

Product 1

HCID 19090914Ethyl diethoxymethyl(cyclohexylmethyl)phosphinate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 38 bg of ethyl diethoxymethyl(benzyl)phosphinate in 300 ml of absolute ethanol is treated with 20 g of Raney nickel and the suspension is hydrogenated at 110° C. and 150 bar for 12 hours. After this time the mixture is filtered through celite® and the filtrate is evaporated to dryness. Distillation of the residue in high vacuum gives ethyl diethoxymethyl(cyclohexylmethyl)phosphinate of b.p. 120° (10-2 mbar). 'H-NMR (CDCl3): δ (ppm)=,4.62 (1 H, d, CHP), 4.17 (2 H, m, CH2OP), 3.84+3.69 (2 H, m, 2×CH2OC), 1.88 (3 H, m, CH2P+CH), 1.68 (6 H, m, 3×CH2), 1.30 (13 H, m, 3×CH3 +2×CH2).

Workup

  1. customis hydrogenated at 110° C.
  2. filtrationAfter this time the mixture is filtered through celite®
  3. customthe filtrate is evaporated to dryness
  4. distillationDistillation of the residue in high vacuum

Sources & evidence

ORD record
ord-4d5abce812bd4cf7a5c440fe94a01a0b
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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