Acetyl chloride → Methyl 7-hydroxyhept-5-ynoate

HRID 1814197노트

반응식

HRID 1814197 반응식
C([O:4][CH2:5][C:6]#[C:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])(=O)C.[C:14](Cl)(=O)C.C(=O)(O)[O-].[Na+].C([Si](C)(C)OCCCCC#CCO)(C)(C)C>CO>[CH3:14][O:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]#[C:6][CH2:5][OH:4]

참가 물질

6

반응물 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 111725557-(tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-olHCID 219644197-Acetoxy-hept-5-ynoic acid

생성물 1

HCID 11789443Methyl 7-hydroxyhept-5-ynoate수율 92%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

The crude acid 29 (6.333 g) was treated with a 1% solution of acetyl chloride in methanol (60 mL). After 16 h, sodium bicarbonate (1.966 g, 23.4 mmol) was added. The mixture was dried (MgSO4), filtered through celite and evaporated in vacuo. Purification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes) gave 7-Hydroxy-hept-5-ynoic acid methyl ester 30 (3.022 g, 19.3 mmol, 92% from 7-tert-Butyl-dimethyl-silanyloxy)-hept-2-yn-1-ol 27).

후처리

  1. dry with materialThe mixture was dried (MgSO4)
  2. filtrationfiltered through celite
  3. customevaporated in vacuo
  4. customPurification by flash chromatography on silica gel (30-40% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-580b7f4c5c18410992e72e600c2e7852
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875787B2

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