Ethanol → 2-Oxiranyl,9,10-dihydrophenanthrene

HRID 374550Notes

Reaction equation

HRID 374550 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:17]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1.[BH4-].[Na+].C([OH:22])C>O>[O:22]1[CH2:2][CH:3]1[C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 189972702-Bromoethyl-9,10-dihydrophenanthrene

Product 1

HCID 152892992-Oxiranyl,9,10-dihydrophenanthrene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a boiling solution of 1.51 g (5 mmol) of (28) in ethanol (40 mL), a solution of 285 mg (7,5 mmol) of NaBH4 in 5 mL of water was added dropwise. Boiling was continued for 5 min, the solution was cooled, diluted with water, and extracted with ether. The ether extract was washed with water, dried, and the solvent was removed at reduced pressure to provide (29) as a colorless oil. This soldified on trituration with a few drops of ether to yield (29), m.p. 65°-66° C.

Workup

  1. temperaturethe solution was cooled
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washwas washed with water
  5. customdried
  6. customthe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-d683c5963fe94fddacee06fc09d355ab
Source dataset
uspto-grants-1996_01
Patent number
US05480913

Reaction notes

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