Furfural → HCID 58677818, compound

HRID 747108Notes

Reaction equation

HRID 747108 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([C:16]2[CH:28]=[CH:27][C:19]([C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=2)[N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[CH:34]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[CH2:25]([N:22]([CH2:23][CH3:24])[C:20]([C:19]1[CH:27]=[CH:28][C:16]([CH:9]([N:10]2[CH2:11][CH2:12][N:13]([CH2:34][C:30]3[O:29][CH:33]=[CH:32][CH:31]=3)[CH2:14][CH2:15]2)[C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]#[N:2])=[CH:17][CH:18]=1)=[O:21])[CH3:26]

Participants

6

Reactant 3

HCID 7362FurfuralHCID 5049666Sodium triacetoxyborohydrideHCID 58677815HCID 58677815, compound

Product 1

HCID 58677818HCID 58677818, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of INTERMEDIATE 3 (567 mg) in 1,2-dichloroethane (15 mL) was added 2-furaldehyde (160 μL, 1.3 eq) and sodium triacetoxyborohydride (450 mg, 1.4 eq). After 3 days the reaction was diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate. The aqueous layer was washed with dichloromethane (2×25 mL) and the combined organic extracts were dried (NgSO4), filtered and concentrated. The residue was purified by flash chromatography, eluting 5% methanol in dichloromethane to yield INTERMEDIATE 4b as a colorless foam (367 mg, 53%).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. washThe aqueous layer was washed with dichloromethane (2×25 mL)
  3. customthe combined organic extracts were dried (NgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-a10e287eccb94fefa24b1ded1ffc8123
Source dataset
uspto-grants-2008_07
Patent number
US07396834B2

Reaction notes

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