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

HRID 1640525ノート

反応式

HRID 1640525 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7a7e80d86f9a4360be5daf12737c49a8
出典データセット
uspto-grants-2012_02
特許番号
US08114867B2

反応ノート

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