Allyl bromide → 3-(2-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-pent-4-enoyl)-oxazolidin-2-one

HRID 1108384Notes

Reaction equation

HRID 1108384 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]OC[CH2:20]1.[Li]N([Si](C)(C)C)[Si](C)(C)C.C(Br)C=C>CCOC(C)=O>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH:10]([CH2:23][CH:19]=[CH2:20])[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

6

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 154537573-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoyl]-oxazolidin-2-oneHCID 178418261HCID 178418261, compound

Product 1

HCID 154537583-(2-[3-(2-Methyl-[1,3]dioxolan-2-yl)-propyl]-pent-4-enoyl)-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-3 (6.0 g, 23.3 mmol) and THF (125 mL) at -78° C. was added LiN(TMS)2 (18.9 mL, 37.8 mmol, 1.0M in THF) dropwise over 10 minutes. After 20 minutes, allyl bromide was added. After 10 minutes, the reaction was warmed to 0° C. After 4.0 h, the reaction was diluted with EtOAc, washed with sat. NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 50% EtOAc/hexanes) gave 2-4 as an yellow oil.

Workup

  1. waitAfter 10 minutes
  2. waitAfter 4.0 h
  3. washwashed with sat. NaHCO3, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6298f7af38924d8e90feda4c6451db83
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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