Potassium Carbonate → Cyclohexylmethyl 5-bromofuran-2-carboxylate

HRID 63321

반응식

HRID 63321 반응식
[Br:1][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH:10]1([CH2:16]Br)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[Br:1][C:2]1[O:6][C:5]([C:7]([O:9][CH2:16][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 685115-Bromo-2-furanecarboxylic acidHCID 137636Cyclohexane, (bromomethyl)-2회

생성물 1

HCID 86694615Cyclohexylmethyl 5-bromofuran-2-carboxylate

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A mixture of 5-bromofuran-2-carboxylic acid (2.64 g, 13.8 mmol), (cyclohexylmethyl)bromide (2.62 g, 14.8 mmol), K2CO3 (2.30 g, 16.64 mmol) in anhydrous NMP was stirred under Ar at +70° C. for 8 hrs after which additional (cyclohexylmethyl)bromide (1.55 g, 8.75 mmol) was added. Stirring continued overnight then the reaction mixture was concentrated under reduced pressure. The residue was partitioned between aqueous NaHCO3 (10%) and hexanes, and then aqueous layer was extracted with hexanes. Combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure to give cyclohexylmethyl 5-bromofuran-2-carboxylate as a light yellow oil. Yield (2.22 g, 56%); 1H NMR (400 MHz, CDCl3) δ 7.10 (d, J=3.9 Hz, 1H), 6.44 (d, J=3.4 Hz, 1H), 4.10 (d, J=6.4 Hz, 2H), 1.64-1.84 (m, 6H), 1.12-1.34 (m, 3H), 0.95-1.09 (m, 2H).

후처리

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between aqueous NaHCO3 (10%) and hexanes
  4. extractionaqueous layer was extracted with hexanes
  5. washCombined organic layers were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-49f17556297445d296f005a98aae47f5
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447078B2

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