1,3,3-Trimethyl-2-methyleneindoline → HCID 15868837, compound

HRID 54602

Reaction equation

HRID 54602 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([OH:17])[CH:8]=2)[CH2:3][CH2:2]1.[CH3:18][N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH3:29])([CH3:28])[C:20]1=[CH2:30].[CH2:31](OC(OCC)OCC)C>C(OCC)C>[CH3:18][N:19]1[C:20]2([O:17][C:9]3[CH:8]=[C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[C:16]4[C:11]([C:10]=3[CH:31]=[CH:30]2)=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:21]([CH3:28])([CH3:29])[C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2

Participants

5

Reactant 3

HCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 31214Ethyl orthoformateHCID 109880424-Morpholino-2-naphthol

Product 1

HCID 15868837HCID 15868837, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-morpholino-2-naphthol (0.47 g;0.002 mol), prepared as in 2(b) above, 1,3,3-trimethyl-2-methyleneindole (0.8 g;0.0022 mol) and triethylorthoformate (10.0 ml) was stirred under nitrogen and heated to reflux for 18 hrs. The resulting purple solution was cooled and evaporated to remove the excess triethylorthoformate and the residue flash chromatographed over silica (40% diethyl ether in hexane) to yield an orange gum (0.28 g; yield 34%). Trituration of the gum with diethyl ether afforded the 1,3,3-trimethyl-6'-morpholinospiro [indoline-2,3'-[3H]-naphtho[2,1-b]pyran having the structure shown below as a pale brown solid, m.pt 191°-194° C. ##STR20##

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hrs
  3. temperatureThe resulting purple solution was cooled
  4. customevaporated
  5. customto remove the excess triethylorthoformate
  6. customthe residue flash chromatographed over silica (40% diethyl ether in hexane)
  7. customto yield an orange gum (0.28 g; yield 34%)

Sources & evidence

ORD record
ord-65b5dd14fecf47bd973f6544bcddcf9c
Source dataset
uspto-grants-1997_04
Patent number
US05623005

Linked notes

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