Hydrochloric Acid → 5-Hydroxycyclohex-1-ene-1-carbonitrile

HRID 1852468

反応式

HRID 1852468 の反応式
C([O:5][CH:6]1[CH2:11][CH2:10][CH:9]=[C:8]([C:12]#[N:13])[CH2:7]1)(=O)CC.[OH-].[Na+].Cl>C1COCC1.CCO>[OH:5][CH:6]1[CH2:7][C:8]([C:12]#[N:13])=[CH:9][CH2:10][CH2:11]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867310083-Cyanocyclohex-3-en-1-yl propanoate

生成物 1

HCID 601605645-Hydroxycyclohex-1-ene-1-carbonitrile

試薬・触媒・溶媒 1

HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

To a solution of (R or S)-3-cyanocyclohex-3-en-1-yl propanoate (210 g, 1.17 mol) in 1:1 THF/EtOH (2 L) at 0° C. was added 3M aqueous NaOH (586 mL, 1.76 mol) dropwise via addition funnel over 30 minutes. After addition, The mixture was stirred at ambient temperature for 2 hours. The mixture was carefully neutralized with 3N aqueous HCl (195 mL), concentrated to remove most of the THF/EtOH. The resulting mixture was diluted with brine (1.5 L) and extracted with EtOAc (1.2 L, then 600 mL×4). The combined organics were washed with brine (200 mL×2). The aqueous layer was back-extracted with EtOAc (200 mL×2), and the combined organic extracts were dried over anhydrous Na2SO4, and concentrated in vacuo to give the enantioenriched title compound (chiral HPLC: 98.4% ee). 1H NMR data was consistent with that reported in the literature for racemic 5-Hydroxycyclohex-1-enecarbonitrile.

後処理

  1. additiondropwise via addition funnel over 30 minutes
  2. additionAfter addition
  3. concentrationconcentrated
  4. customto remove most of the THF/EtOH
  5. additionThe resulting mixture was diluted with brine (1.5 L)
  6. extractionextracted with EtOAc (1.2 L
  7. washThe combined organics were washed with brine (200 mL×2)
  8. extractionThe aqueous layer was back-extracted with EtOAc (200 mL×2)
  9. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-76127258e98f47efb4d322c4928716fb
出典データセット
uspto-grants-2015_02
特許番号
US08962608B2

関連ノート

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