Diketene → HCID 23346094, compound

HRID 1856206Notes

Reaction equation

HRID 1856206 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([C:14]([F:17])([F:16])[F:15])([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH2:9][CH2:8]2)[OH:4].[CH2:20]=[C:21]1[O:25][C:23](=[O:24])[CH2:22]1>O1CCCC1>[F:16][C:14]([F:17])([F:15])[C:3]([C:2]([F:1])([F:18])[F:19])([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:23](=[O:24])[CH2:22][C:21](=[O:25])[CH3:20])[CH2:9][CH2:8]2)[OH:4]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 139280132,3-Dihydro-α,α-bis(trifluoromethyl)-1H-indole-5-methanol

Product 1

HCID 23346094HCID 23346094, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 343 g (1.25 mole) of α,α-bis(trifluoromethyl)-2,3-dihydro-1H-indole-5-methanol in 1880 ml of dry tetrahydrofuran cooled in an ice bath is added dropwise 106 g (1.26 mole) of diketene. The solution is allowed to warm to room temperature for 16 hours and then is refluxed for 30 minutes. The solvent is evaporated to give 463 g (100%) of crude α,α-bis(trifluoromethyl)-1-(1,3-dioxobutyl)-2,3-dihydro-1H-indole-5-methanol, m.p. 150°-151°.

Workup

  1. temperatureis refluxed for 30 minutes
  2. customThe solvent is evaporated

Sources & evidence

ORD record
ord-c0430b43079146f4b799134384918532
Source dataset
uspto-grants-1980_08
Patent number
US04218448

Reaction notes

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