Ethyl Acetate → HCID 23093714, compound

HRID 2223756Notes

Reaction equation

HRID 2223756 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

3,4-Diethoxy-2-fluoro-6-formylbenzonitrile (5.90 kg, 24.87 mol) and ethyl acetate (59.0 L) were transferred to a reaction vessel under a nitrogen atmosphere, and while stirring, sodium triacetoxyborohydride (NaB(OAc)3H) (11.70 kg) was added. After 30 minutes of stirring, the internal temperature was heated up to 40° C., and the reaction solution was stirred for another 2 hours. The reaction solution was cooled, and at 15° C. internal temperature, water (2 L) was slowly added in drops, and excess sodium triacetoxyborohydride was degraded. Then more water (27.5 L) was added. The insoluble material was dissolved by increasing the outer bath temperature to 40° C., and the solution was separated after cooling. Following separation, the obtained organic layer was washed twice with an aqueous sodium bicarbonate solution and then with brine. The obtained organic layer was cooled in a 10° C. outer bath, and left to stand overnight.

Workup

  1. stirringAfter 30 minutes of stirring
  2. stirringthe reaction solution was stirred for another 2 hours
  3. temperatureThe reaction solution was cooled
  4. dissolutionThe insoluble material was dissolved
  5. temperatureby increasing the outer bath temperature to 40° C.
  6. customthe solution was separated
  7. temperatureafter cooling
  8. customseparation
  9. washthe obtained organic layer was washed twice with an aqueous sodium bicarbonate solution
  10. temperatureThe obtained organic layer was cooled in a 10° C. outer bath
  11. waitleft

Sources & evidence

ORD record
ord-c0aed101b17c47709dc5575fd6ec424b
Source dataset
uspto-grants-2008_05
Patent number
US07375236B2

Reaction notes

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