Triphenylphosphine → Diethyl (7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine-4-yl)methylenemalonate

HRID 846329Notes

Reaction equation

HRID 846329 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[F:32][C:33]1[C:38]([F:39])=[CH:37][CH:36]=[C:35]([NH:40][CH:41]=[C:42]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[C:43]([O:45][CH2:46][CH3:47])=[O:44])[C:34]=1[O:53][CH2:54][CH:55](O)[CH3:56]>O1CCCC1>[F:39][C:38]1[CH:37]=[CH:36][C:35]2[N:40]([CH:41]=[C:42]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:55]([CH3:56])[CH2:54][O:53][C:34]=2[C:33]=1[F:32]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 146971832,3-Difluoro-6-(2,2-diethoxycarbonylethenyl)amino-[(2-hydroxypropyl)oxy]benzene

Product 1

HCID 13364401Diethyl (7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine-4-yl)methylenemalonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 341 mg of triphenylphosphine in 5 ml of anhydrous tetrahydrofuran was added dropwise 226 mg of diethyl azodicarboxylate and the mixture was stirred under cooling with ice for 20 minutes. To this solution was added a solution of 373 mg of the compound obtained in Example 3 in 3 ml of anhydrous tetrahydrofuran, and the mixture was stirred at room temperature overnight.

Workup

  1. temperatureunder cooling with ice for 20 minutes
  2. stirringthe mixture was stirred at room temperature overnight

Sources & evidence

ORD record
ord-e70bf8acb0d14364a763a85e765857dc
Source dataset
uspto-grants-1992_08
Patent number
US05136059

Reaction notes

Loading…