4-Acetylbutyric acid → Pentafluorophenyl 5-oxohexanoate

HRID 1453979

Reaction equation

HRID 1453979 reaction equation
[O:1]=[C:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].C(N(CC)C(C)C)(C)C.FC(F)(F)C(O[C:24]1[C:29]([F:30])=[C:28]([F:31])[C:27]([F:32])=[C:26]([F:33])[C:25]=1[F:34])=O>C(Cl)Cl>[O:1]=[C:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6]([O:8][C:24]1[C:25]([F:34])=[C:26]([F:33])[C:27]([F:32])=[C:28]([F:31])[C:29]=1[F:30])=[O:7]

Participants

5

Reactant 3

HCID 184074-Acetylbutyric acidHCID 81531DiisopropylethylamineHCID 4327891Pentafluorophenyl Trifluoroacetate

Product 1

HCID 86609189Pentafluorophenyl 5-oxohexanoateYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Oxohexanoic acid (2.6 g; 20 mmol) was dissolved in CH2Cl2 (50 mL). N,N-Diisopropylethylamine (10.4 mL, 60 mmol) was added followed by pentafluorophenyl trifluoroacetate (3.61 mL; 21 mmol). The reaction mixture was kept at room temperature for 1 hour and evaporated. The residue was resuspended in EtOAc:Hexanes (1:1) and loaded on a silica gel column (5×20 cm) equilibrated and developed with the same mixture. Fractions containing the product (14) (Rf˜0.7) were pooled and concentrated to give 4.7 g (79%) of yellowish oil after drying in vacuum. 1H NMR (CDCl3) δ 2.05 (m, 2H), 2.18 (s, 3H), 2.61 (t, 2H), 2.74 (t, 2H).

Workup

  1. customevaporated
  2. additionFractions containing the product (14) (Rf˜0.7)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9c7fa08c558c4dcab32dedbbae5a14d7
Source dataset
uspto-grants-2009_01
Patent number
US07476735B2

Linked notes

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