Acetyl chloride → Methyl 7-hydroxyhept-5-ynoate

HRID 1814197Notes

Reaction equation

HRID 1814197 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-580b7f4c5c18410992e72e600c2e7852
Source dataset
uspto-grants-2005_04
Patent number
US06875787B2

Reaction notes

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