Sodium Chloride → 3-(4-Methyl-tetrahydro-pyran-4-yl)-3-oxo-propionic acid ethyl ester

HRID 2075802Notes

Reaction equation

HRID 2075802 reaction equation
B(F)(F)F.CCOCC.[N+](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-].[CH3:18][C:19]1([CH:25]=[O:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[Na+].[Cl-]>C(Cl)Cl>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][C:25]([C:19]1([CH3:18])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:26])[CH3:17]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8000Boron trifluoride etherateHCID 12192Ethyl diazoacetateHCID 205923884-Methyloxane-4-carbaldehyde

Product 1

HCID 597772673-(4-Methyl-tetrahydro-pyran-4-yl)-3-oxo-propionic acid ethyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of BF3.OEt2 (0.350 mL, 2.50 mmol) and ethyl diazoacetate (0.390 mL, 3.42 mmol) was added a solution of 4-methyl-tetrahydro-pyran-4-carboxaldehyde (350 mg, 2.73 mmol) in CH2Cl2 (15 mL). After 20 min, the mixture was poured into half-saturated aq. NaCl and extracted with CH2Cl2. The combined organic layers were dried and concentrated. Chromatography (EtOAc/hexanes) afforded the title compound (461 mg, 79%) as a colorless oil. MS (ESI): mass calcd. for C11H18O4, 214.1; m/z found, 215.2 [M+H]+. 1H NMR (mixture of tautomers; CDCl3): 12.5 (s, 0.5H), 5.05 (s, 0.5H), 4.25-4.17 (m, 2H), 3.76-3.53 (m, 2H), 5.52 (s, 3H), 2.05-1.92 (m, 2H), 1.56-1.47 (m, 2H), 1.26-1.22 (m, 3H), 1.38-1.34 (m, 3H).

Workup

  1. extractionextracted with CH2Cl2
  2. customThe combined organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-35ad202ef3924b9a90ec11d1addf34a2
Source dataset
uspto-grants-2011_04
Patent number
US07923451B2

Reaction notes

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