Toluene → 5'-(2-Formylvinyl)-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho [2,1-b][1,4]oxazine]

HRID 376213Notes

Reaction equation

HRID 376213 reaction equation
C([C:3]1[C:12]2[O:13][C:14]3([C:24]([CH3:26])([CH3:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]3[CH3:27])[CH:15]=[N:16][C:11]=2[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=O.C1(P(=[CH:47][CH:48]=[O:49])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:50]1(C)C=CC=CC=1>>[CH:48]([CH:47]=[CH:50][C:3]1[C:12]2[O:13][C:14]3([C:24]([CH3:25])([CH3:26])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]3[CH3:27])[CH:15]=[N:16][C:11]=2[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=[O:49]

Participants

4

Reactant 3

HCID 1140TolueneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 153056895'-Formyl-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Product 1

HCID 543991255'-(2-Formylvinyl)-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho [2,1-b][1,4]oxazine]

Procedure

A solution of 0.36 g (1 mmol) of the compound of Example 1 and of 0.30 g (1 mmol) of (triphenylphosphoranylidene)acetaldehyde in 10 ml of toluene is heated to reflux for 24 hours. The solvent is then evaporated off and the mixture purified on a silica column (70/30 pentane/ether eluent).

Workup

  1. temperatureto reflux for 24 hours
  2. customThe solvent is then evaporated off
  3. customthe mixture purified on a silica column (70/30 pentane/ether eluent)

Sources & evidence

ORD record
ord-e21c2f9b8ccb41b1b8d1d3002635d1c9
Source dataset
uspto-grants-2000_02
Patent number
US06019914

Reaction notes

Loading…