4-Hydroxybenzaldehyde → HCID 21712645, compound

HRID 650579Notes

Reaction equation

HRID 650579 reaction equation
[CH3:1][C:2]1[C:3]([CH:16]([OH:18])[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[C:51]1[CH:58]=[CH:57][C:54]([CH:55]=[O:56])=[CH:53][CH:52]=1>C1COCC1.O>[CH3:1][C:2]1[C:3]([CH:16]([O:18][C:51]2[CH:58]=[CH:57][C:54]([CH:55]=[O:56])=[CH:53][CH:52]=2)[CH3:17])=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 4983340HCID 4983340, compound

Product 1

HCID 21712645HCID 21712645, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol (246 mg; 1.0 mmol), triphenylphosphine (262 mg; 1.0 mmol), diethyl azodicarboxylate (0.153 ml; 1.0 mmol) and 4-hydroxybenzaldehyde (183 mg; 1.5 mmol) in THF (20 ml) was stirred at 0° C. for 1.5 hours and for 16 hours at room temperature. Water was added (20 ml) and the mixture was extracted with methylene chloride (3×25 ml). The combined organic phases were dried and evaporated. The residue was purified on column chromatography using ethyl acetate: hexane (1:3) as eluent. Yield 180 mg.

Workup

  1. extractionthe mixture was extracted with methylene chloride (3×25 ml)
  2. customThe combined organic phases were dried
  3. customevaporated
  4. customThe residue was purified on column chromatography

Sources & evidence

ORD record
ord-5220766a7d9f4af9b708089b5c47a20f
Source dataset
uspto-grants-2001_08
Patent number
US06274608B1

Reaction notes

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