Pivaloyl chloride → HCID 66934181、化合物

HRID 1019619ノート

反応式

HRID 1019619 の反応式
[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

参加物

6

反応物 3

HCID 62493Pivaloyl chlorideHCID 58256121HCID 58256121、化合物HCID 178418339Butyllithium

生成物 1

HCID 66934181HCID 66934181、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b12e3e10cbf94e50b39668ebc6fc31b8
出典データセット
uspto-grants-2014_05
特許番号
US08716276B2

反応ノート

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