تفاعل #1483108

ord-7720d39a9e1b424fa867ae05d833f18e

معادلة التفاعل

CC(C)(Br)C(=O)Br
2-bromo-2-methylpropionyl bromide
CCCCCCCCCCCC(C)O
tridecan-2-ol
CCCCCCCCCCCC(C)O
2-tridecanol
CCN(CC)CC
triethylamine
C=C(CCCCCCCCCCC)OC(=O)C(C)Br
98
المردود 97.6%
C=C(CCCCCCCCCCC)OC(=O)C(C)Br
tridecen-2-yl 2-bromopropanoate
المردود 97.6%

المذيبات

ظروف التفاعل

درجة الحرارة
57.5°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe reaction mixture was quenched with saturated sodium bicarbonate solution
  2. 2
    workup.STIRRINGstirred for 15 minutes at 25-35° C
  3. 3
    أخرىThe aqueous and organic layers were separated
  4. 4
    غسيلThe organic layer was washed with brine
  5. 5
    غسيلthe combined organic layers were washed with brine solution
  6. 6
    تجفيفThe organic layer was dried over Na2SO4
  7. 7
    تركيزconcentrated under vacuum

الإجراء التجريبي

To a stirred solution of tridecan-2-ol 68 (5 g, 24.9 mmol) in toluene (50 mL) was added triethylamine (3.5 mL, 27.45 mmol)) and followed by 2-bromo-2-methylpropionyl bromide 97 (6.31 g, 27.45 mmol) at 5-10° C. The reaction mixture was stirred for 3 hour at 55-60° C., and the reaction was monitored by TLC. The reaction mixture was quenched with saturated sodium bicarbonate solution and stirred for 15 minutes at 25-35° C. The aqueous and organic layers were separated. The organic layer was washed with brine, and the combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 98 (8.1 g, yield: 96%) as a liquid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08900625B2uspto-grants-2014_12