Acetic Anhydride → HCID 19965633, compound

HRID 977276Notes

Reaction equation

HRID 977276 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:25])=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])=[CH:15][CH:14]=2)[N:10]=1.[C-:26]#[N:27].[Na+].[C:29]([O:32]C(=O)C)(=O)[CH3:30]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl>[C:29]([O:24][CH:23]([CH2:22][CH2:21][CH2:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][C:9]2[N:10]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[O:7][C:8]=2[CH3:25])=[CH:18][CH:17]=1)[C:26]#[N:27])(=[O:32])[CH3:30]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8929Sodium CyanideHCID 19965659HCID 19965659, compound

Product 1

HCID 19965633HCID 19965633, compound

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

After a mixture of 5-[4-[2-[2-(2-furyl)-5-methyl-4-oxazolyl]ethyl]phenyl]pentan-1-al (2.2 g), sodium cyanide (0.383 g), acetic anhydride (0.796 g), benzyltributylammonium chloride (0.608 g) and dichloromethane (40 ml)water (10 ml) was stirred at room temperature for 2 hours, the organic layer was separated, washed with water, dried (MgSO4), and then concentrated under reduced pressure, to yield 2-acetoxy-6-[4-[2-[2-(2-furyl)-5-methyl-4-oxazolyl]ethyl]phenyl]hexanenitrile as an oily substance.

Workup

  1. customthe organic layer was separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-566b297a4e58421b899fb78c9db97a2b
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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