1-Bromo-3-chloropropane → 3-Chloropropyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 335538

반응식

HRID 335538 반응식
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Cl:24][CH2:25][CH2:26][CH2:27]Br.O.O.O.O.O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.CCOC(C)=O.[Cl-].[Na+].O.O.[I-].[Na+]>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:27][CH2:26][CH2:25][Cl:24])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

9

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 1151755-(Tetradecyloxy)-2-furoic acidHCID 86669148Tetrabutylammonium hydroxide pentahydrate

생성물 1

HCID 668698443-Chloropropyl 5-(tetradecyloxy)furan-2-carboxylate수율 69.1%

시약·촉매·용매 5

HCID 5238Sodium Iodide촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

To a vigorously stirred suspension of 5-(tetradecyloxy)furan-2-carboxylic acid (0.650 g, 2.0 mmol) in 10 mL of N,N-dimethylformamide was added 3-chlorobromopropane (0.618 mL, 6.0 mmol), tetrabutylammonium hydroxide pentahydrate (0.734 g, 4.2 mmol) and sodium iodide (˜20 mg). The suspension appeared to go into solution briefly, and then a very finely dispersed white precipitate was observed. The reaction was allowed to stir for 12 hrs. The suspension was then diluted with EtOAc (100 mL), brine (50 mL) and water (50 mL). The phases were separated and the organic phase was washed with water (50 mL) and brine (50 mL). The organic phase was then dried and concentrated to yield 0.554 g of the title compound. This material was used in the subsequent step without further purification.

후처리

  1. customThe phases were separated
  2. washthe organic phase was washed with water (50 mL) and brine (50 mL)
  3. customThe organic phase was then dried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f789956f17f64916aecb4bd78346b715
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884034B2

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