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

HRID 1640525노트

반응식

HRID 1640525 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7a7e80d86f9a4360be5daf12737c49a8
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114867B2

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