Tetrahydrofuran → 3-(2-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-hex-5-enoyl)-oxazolidin-2-one

HRID 322071Notes

Reaction equation

HRID 322071 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([N:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[O:12])[O:6][CH2:5][CH2:4][O:3]1.[CH2:19]1[CH2:23]O[CH2:21][CH2:20]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CCOC(C)=O>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH:10]([CH2:21][CH2:20][CH:19]=[CH2:23])[C:11]([N:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[O:12])[O:6][CH2:5][CH2:4][O:3]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 154537573-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoyl]-oxazolidin-2-one

Product 1

HCID 220088813-(2-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-hex-5-enoyl)-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-3 (3.0 g, 11.7 mmol) and THF (125 mL) at −78° C. was added NaN(TMS)2 (15.2 mL, 15.2 mmol, 1.0 M in THF) dropwise over 20 minutes. Butenyl-4-triflate (5.0 mL, 29.2 mmol) was added dropwise; after 1 h, the reaction was warmed to 0° C. After 1 h, the reaction was diluted with EtOAc, washed with sat. NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 40% EtOAc/hexanes) gave 2-4 as an yellow oil.

Workup

  1. waitAfter 1 h
  2. washwashed with sat. NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-84647aade0b5409190c8790119442840
Source dataset
uspto-grants-2001_04
Patent number
US06211191B1

Reaction notes

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