Hexane → Pentafluorophenyl 2-allyloxymethyl-3-methoxybenzoate

HRID 1754156

반응식

HRID 1754156 반응식
[CH2:1]([O:4][CH2:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])[CH:2]=[CH2:3].[F:17][C:18]1[C:23](O)=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28].C1CCC(N=C=NC2CCCCC2)CC1.CCCCCC>C(OCC)(=O)C>[CH2:1]([O:4][CH2:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([O:10][C:23]1[C:22]([F:25])=[C:21]([F:26])[C:20]([F:27])=[C:19]([F:28])[C:18]=1[F:17])=[O:9])[CH:2]=[CH2:3]

참가 물질

6

반응물 4

HCID 8058HexaneHCID 10868Dicyclohexylcarbodiimide2회HCID 13041PentafluorophenolHCID 598386492-Allyloxymethyl-3-methoxy benzoic acid

생성물 1

HCID 59838640Pentafluorophenyl 2-allyloxymethyl-3-methoxybenzoate수율 110%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매3회

실험 절차

Into a 200 mL round bottom flask was added 6.6 g (0.0297 mol) of 2-allyloxymethyl-3-methoxy benzoic acid and 40 mL of ethyl acetate. 24.05 g of a 25% pentafluorophenol (6.01 g, 0.0327 mol) solution in ethyl acetate was added while stirring. The reaction flask was placed into a water bath and while stirring small portions of DCC (6.2 g, 0.030 mol) were added. The stirring continued overnight at room temperature. The reaction was filtered through two Whatman #541 filters to remove the DCU precipitate. The ethyl acetate solution was concentrated to yield 12.8 g (110% yield), indicating presence of DCC and DCU. This was confirmed by TLC (1:1 ethyl acetate:hexane), which indicated a Rf of 0.72 plus other less polar compounds (12 stain indicates about 85% purity). 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.7 (d, 1H), 7.45 (t, 1H), 7.15 (d, 1H), 6.0-5.9 (m, 1H), 5.3-5.1 (2 d, 2H), 4.88-4.83 (d, 2H), 4.06 (d, 2H), 3.90 (s, 3H).

후처리

  1. customThe reaction flask was placed into a water bath
  2. additionwere added
  3. customThe stirring continued overnight
  4. customat room temperature
  5. filtrationThe reaction was filtered through two Whatman #541 filters
  6. customto remove the DCU precipitate
  7. concentrationThe ethyl acetate solution was concentrated
  8. customto yield 12.8 g (110% yield)

출처 및 근거

ORD 기록
ord-baa2ef02af7d4ebe83aa29d9c0a07e41
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169210B2

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