Pivaloyl chloride → HCID 66934181, 화합물

HRID 1019619노트

반응식

HRID 1019619 반응식
[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([Cl:19])=[C:16](Cl)[S:17][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH3:25][C:26]([CH3:31])([CH3:30])[C:27](Cl)=[O:28]>C1COCC1.CCCCCC>[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([Cl:19])=[C:16]([C:27](=[O:28])[C:26]([CH3:31])([CH3:30])[CH3:25])[S:17][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 62493Pivaloyl chlorideHCID 58256121HCID 58256121, 화합물HCID 178418339Butyllithium

생성물 1

HCID 66934181HCID 66934181, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

The product from step (g) (109 mg, 0.35 mmol) in anhydrous THF (5 ml) was cooled to −78° C. under a nitrogen atmosphere and treated with 1.6 M n-butyl lithium in hexane (0.25 ml). The reaction mixture was stirred at −78° C. for 5 minutes followed by the addition of trimethyl acetyl chloride (0.22 ml, 1.75 mmol). After 10 additional minutes at −78° C., the reaction mixture was allowed to warm to room temperature. The reaction was quenched with saturated NaHCO3 (20 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with brine (50 ml), dried (MgSO4), and solvent evaporated in vacuo to give the subtitled compound as an orange oil which was used in the next step without further purification. MS: ESI (positive): 362, 364 (M+H).

후처리

  1. customat −78° C.
  2. temperatureto warm to room temperature
  3. customThe reaction was quenched with saturated NaHCO3 (20 ml)
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. washThe combined organic extracts were washed with brine (50 ml)
  6. dry with materialdried (MgSO4), and solvent
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-b12e3e10cbf94e50b39668ebc6fc31b8
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716276B2

반응 노트

불러오는 중…