3-Hydroxybenzaldehyde → 3-(Cycloheptylmethoxy)benzaldehyde

HRID 875504Notes

Reaction equation

HRID 875504 reaction equation
[CH:1]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=[O:34].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:1]1([CH2:8][O:9][C:30]2[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=2)[CH:33]=[O:34])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 78193CycloheptanemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 866376133-(Cycloheptylmethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of cycloheptylmethanol (5.244 g, 40.9 mmol), triphenylphosphine (10.73 g, 40.9 mmol) and 3-hydroxybenzaldehyde (11) (5.0 g, 40.9 mmol) in THF (50 mL) was added diethyl azodicarboxylate (9.097 g, 44.99 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was concentrated under reduced pressure, and the residue was suspended in 20% diethyl ether-hexanes. Solids were removed by filtration then the mixture was concentrated under reduced pressure. Purification by flash chromatography (5% EtOAc-hexanes) gave 3-(cycloheptylmethoxy)benzaldehyde as a colorless oil. Yield (3.9 g, 41%): 1H NMR (400 MHz, DMSO-d6) δ 9.95 (s, 1H), 7.46-7.51 (m, 2H), 7.39-7.40 (m, 1H), 7.25 (dt, J=6.8, 2.6 Hz, 1H), 3.81 (d, J=6.8 Hz, 2H), 1.88-1.93 (m, 1H), 1.76-1.82 (m, 2H), 1.22-1.68 (m, 10H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customSolids were removed by filtration
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customPurification by flash chromatography (5% EtOAc-hexanes)

Sources & evidence

ORD record
ord-555fe498bd2b4054959b85ddfc699bd9
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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