Ethyl Acetate → HCID 23093714, compound

HRID 244332Notes

Reaction equation

HRID 244332 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:17])=[C:6]([C:9]([CH:15]=[O:16])=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:7]#[N:8])[CH3:2].C(OCC)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[CH2:1]([O:3][C:4]1[C:5]([F:17])=[C:6]([C:9]([CH2:15][OH:16])=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:7]#[N:8])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydride2×HCID 23093710HCID 23093710, compound

Product 1

HCID 23093714HCID 23093714, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

To a reaction vessel, 3,4-diethoxy-2-fluoro-6-formylbenzonitrile (5.90 kg, 24.87 mol) and ethyl acetate (59.0 L) were added under a nitrogen atmosphere, followed by addition of sodium triacetoxyborohydride (NaB(OAc)3H) (11.70 kg) while stirring. After stirring for 30 min, the inside temperature was raised to 40° C., and the reaction solution was stirred for 2 hours. Then, the reaction solution was cooled. Water (2 L) was added thereto slowly and dropwise at the inside temperature of 15° C. to thereby decompose excessive sodium triacetoxyborohydride. Water (27.5 L) was further added thereto. The temperature of the external bath was raised to 40° C. to dissolve insoluble matter, followed by re-cooling and separation of liquid layers. The resultant organic layer was washed with aqueous sodium bicarbonate solution twice and then with saline. The thus obtained organic layer was cooled with the external bath temperature of 10° C. and left overnight.

Workup

  1. stirringAfter stirring for 30 min
  2. stirringthe reaction solution was stirred for 2 hours
  3. temperatureThen, the reaction solution was cooled
  4. customdropwise at the inside temperature of 15° C.
  5. temperatureThe temperature of the external bath was raised to 40° C.
  6. dissolutionto dissolve insoluble matter
  7. temperatureby re-cooling
  8. customseparation of liquid layers
  9. washThe resultant organic layer was washed with aqueous sodium bicarbonate solution twice
  10. temperatureThe thus obtained organic layer was cooled with the external bath temperature of 10° C.

Sources & evidence

ORD record
ord-2155ebbc981143a38a2107935fe046a3
Source dataset
uspto-grants-2014_02
Patent number
US08658620B2

Reaction notes

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