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tert-Butyl methyl ether → 2-Methyl-5-[4,4,4-trifluoro-3-hydroxy-3-(3,4,5-trichloro-phenyl)-butyryl]-furan-3-carboxylic acid methyl ester

HRID 68576
Notes
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Reaction equation

HRID 68576 reaction equation
[H-].[Li+].[F:3][C:4]([F:17])([F:16])[C:5]([C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[C:9]([Cl:15])[CH:8]=1)=[O:6].[CH3:18][O:19][C:20]([C:22]1[CH:26]=[C:25]([C:27](=[O:29])[CH3:28])[O:24][C:23]=1[CH3:30])=[O:21].CC(OC)(C)C>C1COCC1>[CH3:18][O:19][C:20]([C:22]1[CH:26]=[C:25]([C:27](=[O:29])[CH2:28][C:5]([OH:6])([C:7]2[CH:8]=[C:9]([Cl:15])[C:10]([Cl:14])=[C:11]([Cl:13])[CH:12]=2)[C:4]([F:3])([F:16])[F:17])[O:24][C:23]=1[CH3:30])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 62714Lithium hydrideHCID 10866962Methyl 5-acetyl-2-methylfuran-3-carboxylateHCID 580775942,2,2-Trifluoro-1-(3,4,5-trichlorophenyl)ethan-1-one

Product 1

HCID 867066502-Methyl-5-[4,4,4-trifluoro-3-hydroxy-3-(3,4,5-trichloro-phenyl)-butyryl]-furan-3-carboxylic acid methyl esterYield 123.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiH (1.76 g) is added to a solution of 2,2,2-trifluoro-1-(3,4,5-trichloro-phenyl)-ethanone (35.33 g) and 5-acetyl-2-methyl-furan-3-carboxylic acid methyl ester (20 g) in THF (300 ml). After 1 hour 30 at 60° C. MTBE is added (450 ml) and the reaction mixture is poured onto water (750 ml) at 0° C. The organic phase is washed with water and a saturated aqueous solution of NaCl dried over MgSO4 and concentrated in vacuo to yield 62.3 g of 2-methyl-5-[4,4,4-trifluoro-3-hydroxy-3-(3,4,5-trichloro-phenyl)-butyryl]-furan-3-carboxylic acid methyl ester. The crude product is used without further purification. MS (HPLC/MS): 459 (MH+).

Workup

  1. additionthe reaction mixture is poured onto water (750 ml) at 0° C
  2. washThe organic phase is washed with water
  3. dry with materiala saturated aqueous solution of NaCl dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-902876f080bc48ad8e0deb56ed5f2e12
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822466B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes