Sodium borohydride → HCID 22650022, compound

HRID 393302Notes

Reaction equation

HRID 393302 reaction equation
[CH2:1]=[C:2]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]2[CH2:8][CH2:7][C:6](=O)[C:5]=2[C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]1=2.[BH4-].[Na+]>C(Cl)Cl.CO.O.C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]=[C:2]1[C:3]2[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=2[C:5]2[CH:6]=[CH:7][CH2:8][C:9]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=2

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 22650019HCID 22650019, compound

Product 1

HCID 22650022HCID 22650022, compoundYield 68.1%

Reagents, catalysts & solvents 4

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolventHCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of the ketone 6 (1.0 g, 4.0 mmol) in methylene chloride/methanol (3/1 by volume, 40 mL) was added sodium borohydride (1.0 g, 27 mmol). The reaction was monitored by thin layer chromatography (tlc) for the disappearance of the starting ketone, 6. After 1 hr the reaction was worked up diluting with water (30 mL) and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield a yellow solid. The yellow solid as dissolved in benzene (50 mL) containing p-toluenesulfonic acid (10 mg) and heated to 45° C. The reaction mixture was monitored by tlc for the disappearance of the alcohol (45 min). The reaction was worked up by washing with saturated aqueous sodium bicarbonate solution (30 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield 0.66 g (68 percent) of the 8-methylene-1,8-dihydrodibenzo[e,h]azulene, 7, as a yellow oil.

Workup

  1. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customto yield a yellow solid
  4. washby washing with saturated aqueous sodium bicarbonate solution (30 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba9cfbe78434492596ed91cf333c7902
Source dataset
uspto-grants-2004_10
Patent number
US06806327B2

Reaction notes

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