Phosphoric Acid → 6-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1591210

반응식

HRID 1591210 반응식
[C-]#N.[Na+].Br[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10](=[O:15])[CH2:9][CH2:8]2.OP(O)(O)=O.BrC1CCC2C(=CC=CC=2)C1=O.[C:33](C1CCC2C(=CC=CC=2)C1=O)#[N:34]>C1(C)C=CC=CC=1.O.CC#N>[C:33]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C:10](=[O:15])[CH2:9][CH2:8]2)#[N:34]

참가 물질

9

반응물 5

HCID 1004Phosphoric AcidHCID 8929Sodium CyanideHCID 1011201(2H)-Naphthalenone, 2-bromo-3,4-dihydro-HCID 27335536-Bromo-2-tetraloneHCID 12231027HCID 12231027, 화합물

생성물 1

HCID 162445046-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

A flame dried 1 liter round bottom flask with argon inlet, digital thermometer, and magnetic stir bar, was charged with a 68% NaCN/alumina mixture (21.22 g, 433 mmol)(NaCN and alumina were ground together in a morter and pestle according to the procedure of Dalton et al. J. Org. Chem., 44, (24) 4443(1979)), and tetrakis (triphenylphospine) palladium(0) (10.0 g, 8.65 mmol). The flask was purged three times via vacuum with argon and a solution of 6-bromo-2-tetralone (19.46 g, 86.5 mmol) in degassed toluene (400 mL) was added. The mixture was heated to 80° C. and stirred for 64 hrs at that temperature. Analysis by HPLC indicated 89% conversion (HPLC conditions, column: Waters C18 Bondapak, eluent: 80:20 (0.1% H3PO4 in H2O: CH3CN), flow: 2 mL/min, wavelength: 220 nm, Rt: bromotetralone =9.65 min, cyanotetralone=3.46 min). The reaction was cooled and the mixture filtered through silica gel (elution with 60% ethyl acetate in hexane.) Concentration of the appropriate fractions gave 9.4 g (68%) of 6-cyano-2-tetralone (98.7% by HPLC).

후처리

  1. customA flame dried 1 liter round bottom flask with argon inlet
  2. customThe flask was purged three times via vacuum with argon
  3. temperatureThe reaction was cooled
  4. filtrationthe mixture filtered through silica gel (elution with 60% ethyl acetate in hexane.) Concentration of the appropriate fractions

출처 및 근거

ORD 기록
ord-62efd930a94c464ebc0d4e6077652372
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05206240

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