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

HRID 2229432Notes

Reaction equation

HRID 2229432 reaction equation
[C:1]([CH:3]1[C:6]2[CH:7]=[C:8]([NH2:11])[CH:9]=[CH:10][C:5]=2[CH2:4]1)#[N:2].[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>[C:1]([CH:3]1[C:6]2[CH:7]=[C:8]([NH:11][CH2:15][CH:14]([O:17][CH3:18])[O:13][CH3:12])[CH:9]=[CH:10][C:5]=2[CH2:4]1)#[N:2]

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 1-cyano-5-aminobenzocyclobutane 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, then 16 ml of acetic acid and finally, in fractions, 39.7 g of sodium triacetoxyborohydride. After increasing the temperature to 29° C., the mixture is cooled again to room temperature, and then stirred for 1 hour 15 minutes and hydrolysed by pouring into 500 ml of an aqueous saturated sodium hydrogen carbonate solution. The organic phase is separated off, washed with water and concentrated under reduced pressure to yield the desired product in a quantitative yield.

Workup

  1. additionthere are added rapidly
  2. temperaturethe mixture is cooled again to room temperature
  3. customThe organic phase is separated off
  4. washwashed with water
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce5b56a9116a4a6092739c9ed3ba5bb0
Source dataset
uspto-grants-2002_07
Patent number
US06420413B2

Reaction notes

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