تفاعل #1483100

ord-664cc1f6a3b64a9daa4236d2b1e3ff18

معادلة التفاعل

CC(Br)C(=O)Br
2-bromo propionyl bromide
CCCCCCCCCCCCO
1-decanol
CCCCCCCCCCCCO
1-dodecanol
CCN(CC)CC
triethylamine
CCCCCCCCCCCCOC(=O)C(C)Br
59
المردود 94.0%
CCCCCCCCCCCCOC(=O)C(C)Br
dodecyl 2-bromopropanoate
المردود 94.0%

الكواشف

لا شيء

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 1-decanol 2 (10 g, 53.7 mmol) in toluene (100 mL) was added triethylamine (7.5 mL, 53.7 mmol)), followed by 2-bromo propionyl bromide 58 (12.7 g, 59.1 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 59 (16.2 g, yield: 94%) as a liquid.

المصدر

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