Ethanol → HCID 68839849, compound

HRID 1983575Notes

Reaction equation

HRID 1983575 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:18]=1.C(O)C.[N+](C(OCC)=O)(C(OCC)=O)=[N-]>C(OCC)(=O)C>[CH2:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 14357405DiethyldiazodicarboxylateHCID 58828406HCID 58828406, compound

Product 1

HCID 68839849HCID 68839849, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of the product of step 2 (0.742 g, 3.51 mmol), triphenylphosphine (1.01 g, 3.85 mmol) and ethanol (0.25 mL, 4.29 mmol) in ethyl acetate (12 mL) was added, dropwise, diethyl diazodicarboxylate (0.61 mL, 3.87 mmol). After 4 hours the reaction solution was diluted with ethyl acetate and washed with aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate) and concentrated. The resulting gum was purified by flash chromatography over silica (hexanes/ethyl acetate) to afford 0.744 g (89%) of product as a white solid: 1H NMR (CDCl3) δ7.40 (dd, J=8.4, 2.0 Hz, 1H), 7.37-7.31 (m, 2H), 7.17 (d, J=2.0 Hz, 1H), 7.13 (t, J=7.4 Hz, 1H), 7.03-6.92 (m, 3H), 4.13 (q, J=7.1 Hz, 2H), 1.37 (t, J=7.1 Hz, 3H) ppm.

Workup

  1. washwashed with aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe resulting gum was purified by flash chromatography over silica (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-c49d31c65dcd47e689fc0bf82869a734
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

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