Trifluoroacetic acid → HCID 12604610, compound

HRID 1062017Notes

Reaction equation

HRID 1062017 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].C[Si]([C:13]([Si](C)(C)C)(C([O-])=O)[C:14]([O-:16])=[O:15])(C)C.[Li][CH2:25][CH2:26][CH2:27]C.[C:29]([OH:35])([C:31](F)(F)F)=[O:30]>CCOCC.C(OC(C)=C)(=O)C>[O:7]=[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:13][C:14]([OH:16])=[O:15].[CH3:27][C:26]1([CH3:25])[O:35][C:29](=[O:30])[CH:31]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[O:7]1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 789282-Thiophenecarbonyl chlorideHCID 222245802,2-Bis(trimethylsilyl)propanedioateHCID 178418339Butyllithium

Product 2

HCID 12604610HCID 12604610, compoundHCID 222247082,2-Dimethyl-6-thiophen-2-yl-[1,3]dioxin-4-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7916Isopropenyl acetateSolvent

Procedure

The 3-oxo-3-thiophen-2-yl-propionic acid was prepared from thiophene-2-carbonyl chloride (5.3 mL, 50 mmol) and bis(trimethylsilyl)malonate (25.6 mL, 100 mmol) with n-BuLi (1.6M in hexane, 62.5 mL) in ether at −60° C. to 0° C. according to the general procedure H (method c2). The crude material (7.88 g) was transformed into the title compound by stirring in isopropenyl acetate and TFA according to the general procedure J (method a). Obtained as a yellow solid (4.09 g).

Sources & evidence

ORD record
ord-fe557db6649d4c1b8da738062f541ce8
Source dataset
uspto-grants-2005_11
Patent number
US06960578B2

Reaction notes

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