Triethylamine → HCID 15386793, compound

HRID 2379536Notes

Reaction equation

HRID 2379536 reaction equation
[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:15])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:14])=[CH:11]/[CH:12]=[O:13].C(N(CC)CC)C.[P:24]([O-:29])([O:27][CH3:28])[O:25][CH3:26]>C(#N)C>[OH:13][CH:12]([P:24](=[O:29])([O:27][CH3:28])[O:25][CH3:26])/[CH:11]=[C:10](\[CH3:14])/[CH2:9][CH2:8]/[CH:7]=[C:6](\[CH3:15])/[CH2:5][CH2:4][CH:3]=[C:2]([CH3:16])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienalHCID 21884954Dimethylphosphite

Product 1

HCID 15386793HCID 15386793, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of farnesal (245 mg, 1.11 mmol) in acetonitrile (1.1 ml) under argon at room temperature (r.t), was added triethylamine (0.31 ml, 2.22 mmol) and dimethyl phosphite (0.153 ml, 1.67 mmol) and the resulting mixture stirred at r.t. for 24 hr. The reaction mixture was concentrated in vacuo, the resulting residue was chromatographed over silica gel eluted with ethyl acetate to afford the title compound as a colorless oil: NMR (CDCl3) δ 1.60 (6H, s), 1.68 (3H, s), 1.71 (3H, d, J=3.1 Hz), 1.80-2.30 (9H, m), 3.80 (6H, m), 4.69 (1H, dt, J=9 and 5.4 Hz), 5.00-5.20 (2H, m), 5.34 (1H, m).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue was chromatographed over silica gel
  3. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-cb39564fe9c743b59be7ff1015930761
Source dataset
uspto-grants-1994_11
Patent number
US05362906

Reaction notes

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