Acetyl chloride → Methyl 7-hydroxyhept-5-ynoate

HRID 1749232노트

반응식

HRID 1749232 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+]>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

5

반응물 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 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-1439f3b73b9d43bf87557976cd6044f5
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156810B2

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