Cerium(III) chloride → 4-Hydroxycyclohex-1-ene-1-carbonitrile

HRID 1852466노트

반응식

HRID 1852466 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([C:8]#[N:9])=[CH:4][CH2:3]1.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>CO.O>[OH:1][CH:2]1[CH2:7][CH2:6][C:5]([C:8]#[N:9])=[CH:4][CH2:3]1

참가 물질

6

반응물 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 189737114-Oxocyclohex-1-ene-1-carbonitrile

생성물 1

HCID 867293624-Hydroxycyclohex-1-ene-1-carbonitrile

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

실험 절차

To a stirred solution of 4-oxocyclohex-1-ene-1-carbonitrile (170 mg, 1.40 mmol) in MeOH (2.3 mL) at −78° C. was added cerium (III) chloride (484 mg, 1.96 mmol) in MeOH (4.7 mL). The resulting mixture was allowed to stir for 5 minutes at −78° C. before NaBH4 (48 mg, 1.3 mmol) was added in one portion. The mixture was stirred for 20 minutes and then allowed to warm to ambient temperature. After being stirred for 30 minutes, the reaction mixture was diluted with water and extracted with diethyl ether (3×). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo (23° C. water bath) to afford the title compound. 1H NMR (600 MHz, CDCl3): δ 6.50 (tt, J=3.9, 1.8, 1H), 4.03-3.98 (m, 1H), 3.50-3.42 (qd, J=11.4, 4.5, 1H), 2.50 (br d, J=19.2, 1H), 2.46-2.38 (m, 1H), 2.33-2.23 (m, 1H), 2.21-2.13 (m, 1H), 1.90-1.84 (m, 1H), 1.76-1.67 (m, 1H).

후처리

  1. additionwas added in one portion
  2. stirringAfter being stirred for 30 minutes
  3. extractionextracted with diethyl ether (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo (23° C. water bath)

출처 및 근거

ORD 기록
ord-ab84e98494b84ca09e0986fa2978da12
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962608B2

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