2,2,2-Trifluoroethanol → HCID 49842658, 화합물

HRID 57205

반응식

HRID 57205 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].C1(N=C=NC2CCCCC2)CCCCC1.[F:39][C:40]([F:44])([F:43])[CH2:41]O.CCOC(C)=O>C(Cl)Cl>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:41][C:40]([F:44])([F:43])[F:39])=[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

6

반응물 4

HCID 64092,2,2-TrifluoroethanolHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 1151755-(Tetradecyloxy)-2-furoic acid

생성물 1

HCID 49842658HCID 49842658, 화합물수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred, room temperature suspension of 5-(tetradecyloxy)furan-2-carboxylic acid (1.3 g, 4.0 mmol) in CH2Cl2 (40 mL) was added N,N′-dicyclohexylcarbodiimide (0.990 g, 4.8 mmol), N,N-dimethylaminopyridine (0.488 g, 4.0 mmol) and 2,2,2-trifluoroethanol (0.875 mL, 12.0 mmol). The flask was capped and stirring was continued for 16 hrs at which time TLC (10% EtOAc in Hexanes Rf=0.05 (SM) and 0.25 (Prod)) indicated complete consumption of the starting material. The resulting suspension was diluted with CH2Cl2 (40 mL), filtered and concentrated. This crude material was purified by flash chromatography eluting with 5-20% EtOAc in Hexanes. The resulting solid was further purified by recrystallization in 30 mL of hot 2-propanol with the addition of a minimum amount of water to yield 1.13 g (70%) of the title compound as white needles. MS (m/z, ES−): 406.0 (M−1, 100%); EA found for C23H36F3NO2: C, 62.20; H, 8.18; calcd: C, 62.05; H, 8.18; 1H NMR (400 MHz, DMSO-d6) δ: 7.4 (d, 1H), 5.7 (d, 1H), 4.9 (q, 2H), 4.2 (t, 2H), 1.50-1.57 (m, 2H), 1.10-1.20 (m, 22H), 0.85 (t, 3H).

후처리

  1. customThe flask was capped
  2. customconsumption of the starting material
  3. additionThe resulting suspension was diluted with CH2Cl2 (40 mL)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis crude material was purified by flash chromatography
  7. washeluting with 5-20% EtOAc in Hexanes
  8. customThe resulting solid was further purified by recrystallization in 30 mL of hot 2-propanol with the addition of a minimum amount of water

출처 및 근거

ORD 기록
ord-cc023e50ba544f75b58ea0018d1d2e9d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434718B2

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