4-Hydroxybenzaldehyde → HCID 54160560, compound

HRID 898189Notes

Reaction equation

HRID 898189 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.[C:22]1([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:22]1([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 615235-Phenyl-1-pentanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 54160560HCID 54160560, compoundYield 12.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethylazodicarboxylate (0.49 g, 2.8 mmol) in tetrahydrofuran (2 mL) was added to a solution of 4-hydroxybenzaldehyde (0.25 g, 2.05 mmol), 5-phenyl-1-pentanol (0.34 mL, 2.05 mmol) and triphenylphosphine (0.73 g, 2.80 mmol) in tetrahydrofuran (10 mL) at rt. The reaction was stirred for 2 h. The reaction mixture was concentrated in vacuo. Silica gel chromatography eluting with 20% ethyl acetate/hexane yielded 0.070 g of desired product: 1H NMR (500 MHz, CD3OD): δ 9.83 (s, 1H), 7.86 (d, J=8.7 Hz, 2H), 7.25 (t, 2H), 7.14-7.20 (m, 3H), 7.06 (d, J=8.7 Hz, 2H), 4.09 (t, J=6.4 Hz, 2H), 2.65 (t, J=7.7 Hz, 2H), 1.80-1.88 (m, 2H), 1.68-1.75 (m, 2H), 1.49-1.57 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washSilica gel chromatography eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-40e1e1c931434ea78ca1f900cb521ec9
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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