Acetaldehyde, 2,2-dimethoxy- → HCID 15523870, compound

HRID 351917Notes

Reaction equation

HRID 351917 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:8][CH:7]([C:9]#[N:10])[C:6]=2[CH:11]=1.[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH:15]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.COC(C)(C)C.C(O)(=O)C>[CH3:12][O:13][CH:14]([O:17][CH3:18])[CH2:15][NH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:8][CH:7]([C:9]#[N:10])[C:6]=2[CH:11]=1

Participants

8

Reactant 4

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 14204091HCID 14204091, compound

Product 1

HCID 15523870HCID 15523870, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
29 °C

Procedure

To a suspension of 13.5 g of 5-aminobenzocyclobutane-1-carbonitrile in 400 ml of 1,2-dichloroethane there are added rapidly dropwise 26.5 ml of a 45% solution of 2,2-dimethoxyacetaldehyde in tert-butyl methyl ether, followed by 16 ml of acetic acid and then, in portions, 39.7 g of sodium triacetoxyborohydride. After increasing the temperature to 29° C., the reaction mixture is brought to ambient temperature, stirred for 1 hour 15 minutes and then hydrolysed by pouring the mixture into 500 ml of a saturated aqueous solution of NaHCO3. The organic phase is removed, washed with water, and concentrated under reduced pressure to yield the desired product.

Workup

  1. customis brought to ambient temperature
  2. customThe organic phase is removed
  3. washwashed with water
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-36e31cdaa2f049b6bb3bcbba7d8a38df
Source dataset
uspto-grants-2004_06
Patent number
US06743818B2

Reaction notes

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