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

HRID 2045956
Notes
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Reaction equation

HRID 2045956 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[O:23][C:24]([C:28](=[O:30])[CH3:29])=[CH:25][C:26]=1[CH3:27])=[O:21].C(OC)(C)(C)C>C1COCC1.O>[CH3:18][O:19][C:20]([C:22]1[O:23][C:24]([C:28](=[O:30])[CH2:29][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])=[CH:25][C:26]=1[CH3:27])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 62714Lithium hydrideHCID 580775942,2,2-Trifluoro-1-(3,4,5-trichlorophenyl)ethan-1-oneHCID 66587192Methyl 5-acetyl-3-methylfuran-2-carboxylate

Product 1

HCID 866812923-Methyl-5-[4,4,4-trifluoro-3-hydroxy-3-(3,4,5-trichloro-phenyl)-butyryl]-furan-2-carboxylic acid methyl esterYield 106.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiH (0.41 g) is added to a solution of 2,2,2-trifluoro-1-(3,4,5-trichloro-phenyl)-ethanone (6.76 g) and 5-acetyl-3-methyl-furan-2-carboxylic acid methyl ester (4.46 g) in THF (50 ml). After 3 hours at 60° C. methyl tert-butyl ether (MTBE, 20 ml) is added and the reaction mixture is poured into water (20 ml) at 0° C. The organic phase is extracted once with water and a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo to yield 11.9 g of 3-methyl-5-[4,4,4-trifluoro-3-hydroxy-3-(3,4,5-trichloro-phenyl)-butyryl]-furan-2-carboxylic acid methyl ester. The crude product is used without further purification. MS (HPLC/MS): 459 (MH+). Retention time: 2.01 min.

Workup

  1. extractionThe organic phase is extracted once with water
  2. dry with materiala saturated aqueous solution of NaCl, dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-741e2354078547f7af8a4b15d0d877fa
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08592418B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes