Tetrahydrofuran → HCID 86718364, compound

HRID 1518757Notes

Reaction equation

HRID 1518757 reaction equation
C[C:2]([O-:5])([CH3:4])C.[K+].[C:7]([O:11][C:12](=[O:24])[NH:13][C@H:14]([C:19]1[O:20][CH:21]=[CH:22][CH:23]=1)[C@H:15]([CH3:18])[CH:16]=O)([CH3:10])([CH3:9])[CH3:8].C1C[O:28][CH2:27][CH2:26]1>>[CH2:27]([O:28][C:2](=[O:5])[CH:4]=[CH:16][C@@H:15]([CH3:18])[C@H:14]([NH:13][C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:24])[C:19]1[O:20][CH:21]=[CH:22][CH:23]=1)[CH3:26]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxideHCID 46211385HCID 46211385, compound

Product 1

HCID 86718364HCID 86718364, compoundYield 90%

Procedure

To a solution of ethyl 2-triethylphosphono-acetate (2.2 mL, 11 mmol) in THF (30 mL) at 0° C. was added KOtBu (1.01 g, 9.02 mmol) and stirred for 1 hour at room temperature. The mixture was cooled to −78° C. To the mixture was added slowly a solution of 2.12a (0.993 g, 3.92 mmol) in THF (10 mL. The reaction mixture was poured onto a mixture of ice-cold water/Et2O (10 mL/600 mL), washed with brine twice, dried over MgSO4 and concentrated. Purification by silica gel column chromatography (0-50%, EtOAc/heptane) to give 2.12b (1.14 g, 90% yield). MS m/z (M+23) 346.2. 1H NMR (E, major isomer) (400 MHz, CDCl3) δ ppm 1.05 (d, J=6.90 Hz, 2H) 1.07-1.18 (m, 1H) 1.19-1.32 (m, 2H) 1.36-1.46 (m, 2H) 1.44 (s, 4H) 1.55-1.57 (m, 1H) 4.14-4.22 (m, 1H) 5.74-5.85 (m, 1H) 6.14-6.19 (m, 1H) 6.27-6.33 (m, 1H) 6.86 (dd, J=15.70, 8.17 Hz, 1H) 7.26 (s, 1H) 7.31-7.37 (m, 1H).

Workup

  1. temperatureThe mixture was cooled to −78° C
  2. washwashed with brine twice
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification by silica gel column chromatography (0-50%, EtOAc/heptane)

Sources & evidence

ORD record
ord-3aa437e6bca94cb9b0276fc5d45501bd
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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