P-Cresol → 2,3-Dimethoxy-7-[2-(4-methylphenoxy)ethyl]-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione

HRID 2268557Notes

Reaction equation

HRID 2268557 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:10][CH2:9][C:8]2[C:11](=[O:20])[C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[C:14](=[O:15])[C:7]=2[CH2:6][CH2:5]1.[CH:21]1[C:26](O)=[CH:25][CH:24]=[C:23]([CH3:28])[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:17][O:16][C:13]1[C:14](=[O:15])[C:7]2[CH2:6][CH2:5][CH:4]([CH2:3][CH2:2][O:1][C:26]3[CH:25]=[CH:24][C:23]([CH3:28])=[CH:22][CH:21]=3)[CH2:10][CH2:9][C:8]=2[C:11](=[O:20])[C:12]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 2879P-CresolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 183485737-(2-Hydroxyethyl)-2,3-dimethoxy-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione

Product 1

HCID 183486642,3-Dimethoxy-7-[2-(4-methylphenoxy)ethyl]-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dioneYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7-(2-hydroxyethyl)-2,3-dimethoxy-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione (103 mg), p-cresol (118 mg) and triphenylphosphine (121 mg) in THF (2 ml) was added a solution of diethyl azodicarboxylate (87 mg) in THF (1 ml) at room temperature. The reaction mixture was stirred at room temperature for 2 hr and then concentrated in vacuo. The residue was purified by alumina column chromatography (ethyl acetate:hexane=1:10) and then with recrystallization from duisopropylether-hexane to obtain the entitled compound (80 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by alumina column chromatography (ethyl acetate:hexane=1:10)
  3. customwith recrystallization from duisopropylether-hexane

Sources & evidence

ORD record
ord-b1160e63488e4cf7902514e2edfbb45b
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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