HCID 20067563, compound → HCID 20067590, compound

HRID 982351Notes

Reaction equation

HRID 982351 reaction equation
[CH:1]1[C:10]2[C:9]3[CH:11]=[CH:12][C:13]4[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=4[C:15](=[O:16])[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:21][Li]>O1CCCC1.C(OCC)C>[OH:16][C:15]1([CH3:21])[C:8]2[CH:7]=[CH:6][C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:10]=3[C:9]=2[CH:11]=[CH:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]1=2

Participants

5

Reactant 2

HCID 20067563HCID 20067563, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 20067590HCID 20067590, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7H-benzo[4,5]cyclohepta[1,2-a]naphthalen-7-one (1.75 g, prepared by the method of Bergmann et al, J. Org. Chem., 1963, 28, 3341) in dry tetrahydrofuran (40 ml) at 0° C. under nitrogen was added a solution of methyl lithium in diethyl ether (8 ml of 1.4M). After 90 minutes at 0° C. the reaction was quenched by the dropwise addition of water (20 ml) and the reaction mixture extracted into diethyl ether (2×75ml). dried (Na2SO4), filtered and the solvents removed under reduced pressure to give a light brown oil (1.9 g).

Workup

  1. customAfter 90 minutes at 0° C. the reaction was quenched by the dropwise addition of water (20 ml)
  2. extractionthe reaction mixture extracted into diethyl ether (2×75ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-6748efae96ef44e78cdc4ffb1ea7fa7b
Source dataset
uspto-grants-1991_02
Patent number
US04996211

Reaction notes

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