Hydrochloric Acid → HCID 20342248, compound

HRID 2050195Notes

Reaction equation

HRID 2050195 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:11][CH2:10][CH:9]2[CH:12]=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C-:21]#[N:22].[K+]>O1CCCC1.O>[OH:13][CH:12]([CH:9]1[CH2:10][CH2:11][N:8]1[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:21]#[N:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 127171451-(Diphenylmethyl)-2-azetidinecarboxaldehyde

Product 1

HCID 20342248HCID 20342248, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.4 g (5.57 mmoles) of 1-diphenylmethyl-2-formylazetidine in a mixture of 7.5 ml of tetrahydrofuran and 7.5 ml of water is added 0.91 ml (11.14 mmoles) of concentrated hydrochloric acid under cooling and then 0.724 g (11.14 mmoles) of potassium cyanide is added thereto. The mixture is stirred for 2 hours and extracted with 30 ml of ether. The aqueous layer is reextracted with 30 ml of ether. The extract and the above organic layer are combined, washed with water, dried over magnesium sulfate and evaporated under reduced pressure to yield 1.6 g of crude syrupy 2-hydroxy-2-(1-diphenylmethylazetidin-2-yl)acetonitrile in quantitative yield.

Workup

  1. temperatureunder cooling
  2. extractionextracted with 30 ml of ether
  3. extractionThe extract
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3eb79a8d1808445b9cea4af14a66eb6d
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Reaction notes

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