Sodium hydride → HCID 22285400, 화합물

HRID 1062457

반응식

HRID 1062457 반응식
[H-].[Na+].Br[CH2:4][CH:5]1[CH2:7][CH2:6]1.[S:8]1[CH2:13][CH2:12][CH2:11][S:10][CH:9]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C1(C)C=CC=CC=1.CN(C=O)C>[CH:7]1([CH2:6][C:9]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:8][CH2:13][CH2:12][CH2:11][S:10]2)[CH2:5][CH2:4]1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 88552Ethyl 1,3-dithiane-2-carboxylate

생성물 1

HCID 22285400HCID 22285400, 화합물수율 85.9%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a suspension of NaH (95%, 2.8 g, 111 mmol) in dry toluene (120 mL) stirring at 0° C. was dropwise added, over 10 minutes, a solution of bromomethylcyclopropane (15 g, 111 mmol), and ethyl 1,3-dithiane-2-carboxylate (17.77 g, 92.58 mmol) in dry DMF (40 mL). The ice bath was removed and the solution was stirred overnight at rt. Water was added to the solution and the phases were separated. The organic phase was dried over MgSO4, then evaporated to give 19.6 g (50%) of ethyl 2-(cyclopropylmethyl)-1,3-dithiane-2-carboxylate, which was used in the next step without purification. 1H NMR (CDCl3): δ 4.26 (2H, q, J=7.2 Hz), 3.30-3.23 (2H, m), 2.69-2.64 (2H, m), 2.16-2.11 (1H, m), 1.96 (2H, d, J=6.8 Hz), 1.91-1.81 (1H, m), 1.34 (3H, t, J=7.2 Hz), 0.93-0.86 (1H, m), 0.52-0.47 (2H, m), 0.20-0.16 (2H, m).

후처리

  1. additionwas dropwise added, over 10 minutes
  2. customThe ice bath was removed
  3. stirringthe solution was stirred overnight at rt
  4. additionWater was added to the solution
  5. customthe phases were separated
  6. dry with materialThe organic phase was dried over MgSO4
  7. customevaporated

출처 및 근거

ORD 기록
ord-1cc0038cd33940ad9679aa17d7e8acb5
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960601B2

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