Acetyl chloride → Methyl 7-hydroxyhept-5-ynoate

HRID 1814197ノート

反応式

HRID 1814197 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 11789443Methyl 7-hydroxyhept-5-ynoate収率 92%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-580b7f4c5c18410992e72e600c2e7852
出典データセット
uspto-grants-2005_04
特許番号
US06875787B2

反応ノート

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