4-Hydroxybenzaldehyde → HCID 65597488, compound

HRID 1485059Notes

Reaction equation

HRID 1485059 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]1([CH2:13][CH2:14]O)[CH2:12][CH2:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:10]1([CH2:13][CH2:14][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 1376422-Cyclopropylethan-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 65597488HCID 65597488, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-hydroxybenzaldehyde (2.84 g), 2-cyclopropylethanol (2.00 g), triphenylphosphine (6.09 g) and tetrahydrofuran (100 mL), diethyl azodicarboxylate (2.2 mol/L, solution in toluene, 10.5 mL) was added and the mixture was stirred at room temperature for 4 days. After concentrating the reaction mixture under reduced pressure, ethyl acetate (7.50 mL) and n-hexane (143 mL) were added and the mixture was stirred at room temperature for 15 minutes. The precipitate was removed by filtration through Celite (registered trademark). The filtrate was concentrated under reduced pressure and, thereafter, the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-50:50) to give the titled compound as a yellow oil (3.34 g).

Workup

  1. additionwas added
  2. concentrationAfter concentrating the reaction mixture under reduced pressure, ethyl acetate (7.50 mL) and n-hexane (143 mL)
  3. additionwere added
  4. stirringthe mixture was stirred at room temperature for 15 minutes
  5. customThe precipitate was removed by filtration through Celite (registered trademark)
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-50:50)

Sources & evidence

ORD record
ord-cac62ed9d88f48d6a43d8fb83d3b9f60
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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