Hydrochloric Acid → (S)-1,2-Dihydroacenaphthylen-1-ol

HRID 1675380Notes

Reaction equation

HRID 1675380 reaction equation
B1(C)[O:8][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17]C=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H]2N1CCC2.B.C1COCC1.C1(=O)C2=C3C(=CC=C2)C=CC=C3C1.Cl>ClCCl.CO>[C@@H:7]1([OH:8])[C:9]2=[C:10]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH:17]=[CH:18][CH:19]=[C:20]3[CH2:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 752291-AcenaphthenoneHCID 2723981Borane;tetrahydrofuranHCID 9838490(R)-2-Methyl-CBS-oxazaborolidine

Product 1

HCID 6976867(S)-1,2-Dihydroacenaphthylen-1-olYield 20.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

(R)-2-Methyl-CBS-oxazaboro-lidine (50 ml, 1 mol toluene solution) was cooled to −30° C., and a borane-THF complex (250 ml, 1 mol THF solution) was added. The mixture was stirred for 45 min. Acenaphthen-1-one (40 g, 240 mmol) was dissolved in dichloromethane (500 ml) and the solution was added dropwise. The mixture was stirred under cooling (−30° C.) for 2 hr. Then, methanol (80 ml) and 1N-hydrochloric acid (100 ml) were added under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated aqueous ammonium chloride solution, dried over magnesium sulfate, and concentrated to give (S)-1-acenaphthenol (35 g) as pale-yellow crystals.

Workup

  1. additionthe solution was added dropwise
  2. stirringThe mixture was stirred
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water and saturated aqueous ammonium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e1ebea6b0ae4bad9f75a861f53e0319
Source dataset
uspto-grants-2011_08
Patent number
US08003669B2

Reaction notes

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