Iodine → Methyl 3-oxovalerate

HRID 34414

반응식

HRID 34414 반응식
[O:1]=[C:2]([CH2:7][CH3:8])[CH2:3][C:4]([OH:6])=[O:5].II.ClCl.[CH3:13]O>[OH-].[Na+]>[O:1]=[C:2]([CH2:7][CH3:8])[CH2:3][C:4]([O:6][CH3:13])=[O:5]

참가 물질

6

반응물 4

HCID 807IodineHCID 887MethanolHCID 24526ChlorineHCID 4396843-Oxopentanoic acid

생성물 1

HCID 121699Methyl 3-oxovalerate

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

Intermediates of formula 3 are prepared using methods known in the art. See for example U.S. Pat. No. 3,974,275 to Bossert et al., incorporated fully herein by reference. Additionally, certain intermediates of formula 3 are commercially available, e.g., methyl β-aminocrotonate. Under Claisen reaction conditions, acetone is reacted with methyl propionate in the presence of sodium ethoxide, followed by protonation with dilute HCl, to yield 2,4-hexadione (13). The resulting diketone is then oxidized to 3-oxopentanoic acid (14) by treatment with I2 or Cl2 in aqueous NaOH. The resulting acid is esterified with methanol to yield methyl 3-oxopentanoate (15). The ester is then heated with ammonia, removing water during the reaction to yield methyl 3-aminopent-2-eneoate (3).

출처 및 근거

ORD 기록
ord-5c51225de79c4870981c81da5c9b895a
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761420

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