تفاعل #2304287

ord-a9aa2e8f83684304b2355cc1d2ebcf13

معادلة التفاعل

CC1(COCCCCCCBr)COC1
3-[(6-bromohexyloxy)methyl]-3-methyloxetane
CCOC(=O)c1ccc(O)cc1
ethyl 4-hydroxybenzoate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN(C)C=O
dimethylformamide
CCOC(=O)c1ccc(OCCCCCCOCC2(C)COC2)cc1
ethyl 4-[6-(3-methyloxetan-3-ylmethoxy)hexyloxy]benzoate
المردود 80.6%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصThis was extracted with ethyl acetate
  2. 2
    غسيلthe organic layer was washed with aqueous 2 N-sodium hydroxide solution and water in that order
  3. 3
    تجفيفdried with anhydrous magnesium sulfate
  4. 4
    أخرىThe solvent was evaporated away
  5. 5
    أخرىthe resulting residue was purified through silica gel chromatography (elution solvent:toluene/ethyl acetate=8/2)

الإجراء التجريبي

A reaction mixture comprising 84 g of 3-[(6-bromohexyloxy)methyl]-3-methyloxetane, 50 g of ethyl 4-hydroxybenzoate, 50 g of potassium carbonate and 600 ml of dimethylformamide was stirred at 90° C. for 4 hours. Water was added to the reaction mixture and the reaction was stopped. This was extracted with ethyl acetate, and the organic layer was washed with aqueous 2 N-sodium hydroxide solution and water in that order, and then dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was purified through silica gel chromatography (elution solvent:toluene/ethyl acetate=8/2), and 85 g of ethyl 4-[6-(3-methyloxetan-3-ylmethoxy)hexyloxy]benzoate was obtained.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07407691B2uspto-grants-2008_08