Tetrahydrofuran → HCID 19857180, compound

HRID 2073488Notes

Reaction equation

HRID 2073488 reaction equation
[Mg].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:10][CH2:11][CH2:12]Br)=[CH:5][CH:4]=1.[CH2:21]([N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][C:29]1=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[NH4+].[Cl-].[O:37]1CCCC1>>[CH2:21]([N:28]1[CH2:33][CH2:32][C:31]([CH2:12][CH2:11][CH2:10][CH:9]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=2)([OH:37])[CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 937631,1'-(4-Bromobutylidene)bis[4-fluorobenzene]HCID 51700761-Benzyl-2-piperidoneHCID 5462224Magnesium

Product 1

HCID 19857180HCID 19857180, compound

Procedure

A Grignard solution was prepared from 3.17 g (0.132 mol) of magnesium filings and 42.8 g (0.132 mol) of 4,4-bis(4-fluorophenyl)butyl bromide in 85 ml of absolute tetrahydrofuran. A solution of 25 g (0.132 mol) of distilled N-benzylpiperidone in 130 ml of absolute tetrahydrofuran was then added dropwise in the course of 30 minutes and the mixture was subsequently stirred at room temperature for 1.5 hours. The reaction mixture was poured onto 800 ml of ice, 400 ml of saturated NH4Cl solution were added and the mixture was extracted several times with ether. The extracts were dried and concentrated.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted several times with ether
  3. customThe extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a8f3be13790746db8e0fd54cf1a8b961
Source dataset
uspto-grants-1990_04
Patent number
US04918073

Reaction notes

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