Dimethylformamide → 5-[3-(Dibutyl-pentyl-stannanyl)-allyloxymethyl]-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-oxazolidin-2-one

HRID 1640525Notes

Reaction equation

HRID 1640525 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C@H:14]([CH2:16][OH:17])[O:13][C:12]3=[O:18])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[CH2:19]([Sn:23]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:28][CH2:29][CH2:30][CH3:31])[CH:24]=[CH:25][CH2:26]Cl)[CH2:20][CH2:21][CH3:22].[H-].[Na+].[CH3:38]N(C=O)C>>[CH2:19]([Sn:23]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:28][CH2:29][CH2:30][CH2:31][CH3:38])[CH:24]=[CH:25][CH2:26][O:17][CH2:16][CH:14]1[O:13][C:12](=[O:18])[N:11]([C:9]2[CH:8]=[CH:7][C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:10]=2)[CH2:15]1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 66737186(R)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-hydroxymethyl-oxazolidin-2-oneHCID 85134313Tributyl-(3-chloro-propenyl)-stannane

Product 1

HCID 667373055-[3-(Dibutyl-pentyl-stannanyl)-allyloxymethyl]-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-oxazolidin-2-oneYield 53%

Conditions

Temperature
0 °C

Procedure

A solution of rac-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-hydroxymethyl-oxazolidin-2-one (prepared in analogy to Example 1, step 1.i; 0.852 g, 3.4 mmol) and tributyl-(3-chloro-propenyl)-stannane (prepared according to J. Org. Chem. (2000), 65, 7070; 1.2 g, 3.4 mmol) in DMF (20 mL) was cooled to 0° C. and a NaH dispersion (50% in mineral oil, 325 mg, 2 eq.) was added. The mixture was stirred at 0° C. for 30 min and at rt overnight. The volatiles were removed under reduced pressure and the residue partitioned between EA and water. The org. phase was washed with water, dried over MgSO4 and concentrated. The product was purified by FC (Hept/EA 2:1) to give a yellow oil (1.06 g, 53% yield).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue partitioned between EA and water
  3. washphase was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe product was purified by FC (Hept/EA 2:1)

Sources & evidence

ORD record
ord-7a7e80d86f9a4360be5daf12737c49a8
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

Loading…