Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 5'-(2-Methoxycarbonylvinyl)-1,3,3-trimethylspiro-[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

HRID 376210Notes

Reaction equation

HRID 376210 reaction equation
[C:1]([CH:5]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH3:4])=[O:2].[CH:25]([C:27]1[C:36]2[O:37][C:38]3([C:48]([CH3:50])([CH3:49])[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[N:41]3[CH3:51])[CH:39]=[N:40][C:35]=2[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)=O>ClCCl>[CH3:4][O:3][C:1]([CH:5]=[CH:25][C:27]1[C:36]2[O:37][C:38]3([C:48]([CH3:50])([CH3:49])[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[N:41]3[CH3:51])[CH:39]=[N:40][C:35]=2[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)=[O:2]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 153056895'-Formyl-1,3,3-trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Product 1

HCID 537041535'-(2-Methoxycarbonylvinyl)-1,3,3-trimethylspiro-[indoline-2,3'-[3H]-naphtho[2,1-b][1,4]oxazine]

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.34 g (1 mmol) of carbomethoxymethylene triphenylphosphorane and 0.36 g (1 mmol) of the compound of Example 1 are heated to reflux in 20 ml of dichloromethane for 18 hours. The solvent is evaporated off. The product is purified on a silica column (80/20 pentane/ethyl acetate eluent).

Workup

  1. customThe solvent is evaporated off
  2. customThe product is purified on a silica column (80/20 pentane/ethyl acetate eluent)

Sources & evidence

ORD record
ord-09fe213e901847c68a57c664252334fb
Source dataset
uspto-grants-2000_02
Patent number
US06019914

Reaction notes

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