Diketene → HCID 23346106, compound

HRID 1856209Notes

Reaction equation

HRID 1856209 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([C:15]([F:18])([F:17])[F:16])([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]([CH3:14])[CH2:8]2)[OH:4].[CH2:21]=[C:22]1[O:26][C:24](=[O:25])[CH2:23]1>O1CCCC1>[F:16][C:15]([F:18])([F:17])[C:3]([C:2]([F:1])([F:19])[F:20])([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:24](=[O:25])[CH2:23][C:22](=[O:26])[CH3:21])[CH:9]([CH3:14])[CH2:8]2)[OH:4]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 233461261,1,1,3,3,3-hexafluoro-2-(2-methyl-2,3-dihydro-1H-indol-5-yl)-propan-2-ol

Product 1

HCID 23346106HCID 23346106, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6.0 g (0.02 mole) of α,α-bis(trifluoromethyl)-2,3-dihydro-2-methyl-1H-indole-5-methanol in 50 ml of anhydrous tetrahydrofuran is added 1.9 g (0.022 mole) of diketene. After 16 hours at room temperature, the solution is refluxed for one hour. The solvent is evaporated, and the residue is recrystallized from dibutyl ether to give 5.7 g (74%) of α,α-bis(trifluoromethyl)-1-(1,3-dioxobutyl)-2,3-dihydro-2-methyl-1H-indole-5-methanol, m.p. 118°-119°.

Workup

  1. temperaturethe solution is refluxed for one hour
  2. customThe solvent is evaporated
  3. customthe residue is recrystallized from dibutyl ether

Sources & evidence

ORD record
ord-a134ac6b6aad4716a29c1ca2a801f9cd
Source dataset
uspto-grants-1980_08
Patent number
US04218448

Reaction notes

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