Furfuryl Alcohol → HCID 86584185, compound

HRID 1018604Notes

Reaction equation

HRID 1018604 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:6]([N:8]1[CH2:25][CH2:24][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14](=[O:22])[NH:13][C:12]2=[O:23])[CH2:10][CH2:9]1)=[O:7].[C:35]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)[C:55]1[O:59][CH:58]=[CH:57][CH:56]=1.CCOC(/N=N/C(OCC)=O)=O>O1CCOCC1>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:6]([N:8]1[CH2:9][CH2:10][C:11]2([N:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:14](=[O:22])[N:13]([C:58]3[O:59][CH:55]=[CH:56][CH:57]=3)[C:12]2=[O:23])[CH:24]([CH3:35])[CH2:25]1)=[O:7]

Participants

6

Reactant 4

HCID 7361Furfuryl AlcoholHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 18401669HCID 18401669, compound

Product 1

HCID 86584185HCID 86584185, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8-(3,5-Bis-trifluoromethyl-benzoyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decane-2,4-dione (200 mg, 0.41 mmol) was dissolved in dry dioxane (10 mL) and triphenylphosphin (145 mg, 0.54 mmol), furfuryl alcohol (53.1 mg, 0.54 mmol) and diethylazodicarboxylate (40% in toluene, 0.54 mmol) were added sequentially and stirred at room temperature overnight. The solvent was evaporated and the residue was purified by chromatography on silica gel (dichloromethane) to yield the desired product (143 mg, 61%), MS: m/e=566.1 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-3d81cdfdf9ae4e11bc8af9d369466163
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

Loading…