Heptanol → HCID 86642930, compound

HRID 709872Notes

Reaction equation

HRID 709872 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:13](O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C>C1COCC1>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 8129HeptanolHCID 11776TriphenylphosphineHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 97268Di-tert-butyl azodicarboxylate

Product 1

HCID 86642930HCID 86642930, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Hydroxy-2-nitrobenzaldehyde (3.60 g, 0.0215 mol), 1-heptanol (2.50 g, 0.0215 mol) and triphenylphosphine polymer bound (3 mmol/g loading; 9 g, 0.028 mol) were placed in a flask followed by tetrahydrofuran (300 mL, 4 mol). A solution of azodicarboxylic acid di-tert-butyl ester (5.94 g, 0.0258 mol) in THF (15 mL) was then added dropwise at 23° C. The reaction mixture was then allowed to stir for 1 day. Filtered through a celite pad, and the crude mixture was then purified via chromatography (SiO2, 120 g, 0-100% ethyl acetate/hexanes) to give a pure product (3.25 g, 57%). 1H NMR (CHLOROFORM-d) δ: 10.50 (s, 1H), 8.16 (d, J=9.0 Hz, 1H), 7.32 (d, J=3.0 Hz, 1H), 7.14 (dd, J=9.0, 2.8 Hz, 1H), 4.11 (t, J=6.5 Hz, 2H), 1.76-1.92 (m, 2H), 1.42-1.53 (m, 2H), 1.21-1.42 (m, 6H), 0.82-0.99 (m, 3H). MS (M+1): 266.20.

Workup

  1. customwere placed in a flask
  2. filtrationFiltered through a celite pad
  3. customthe crude mixture was then purified via chromatography (SiO2, 120 g, 0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-be35823b68c144e186bc3b0290dddc83
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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