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

HRID 1852466ノート

反応式

HRID 1852466 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ab84e98494b84ca09e0986fa2978da12
出典データセット
uspto-grants-2015_02
特許番号
US08962608B2

反応ノート

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