Triphenylphosphine → 8-Chloro-1-(tetrahydropyran-4-yloxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

HRID 473475Notes

Reaction equation

HRID 473475 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:18]=1.[O:19]1[CH2:24][CH2:23][CH:22](O)[CH2:21][CH2:20]1.P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH:22]4[CH2:23][CH2:24][O:19][CH2:20][CH2:21]4)[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:18]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67359866HCID 67359866, compound

Product 1

HCID 673624498-Chloro-1-(tetrahydropyran-4-yloxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-oneYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For the synthesis of the title compound, 0.45 g (1.7 mmol) of 8-chloro-1-hydroxy-10,11-dihydrodibenzo[a,d]cyclohepten-5-one, 0.28 g (0.0027 mol) of tetrahydropyran-4-ol, 0.77 g (2.9 mmol) of P(Ph)3 and 0.41 g (2.0 mmol) of diisopropyl azodicarboxylate in 2 ml of THF are reacted by method P. C20H19ClO3 (Mr=342.83); yield: 45%

Sources & evidence

ORD record
ord-26541f1f53934afca33467f209ffeacd
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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