2,2,2-Trifluoroethanol → HCID 49842658、化合物

HRID 57205

反応式

HRID 57205 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 49842658HCID 49842658、化合物収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cc023e50ba544f75b58ea0018d1d2e9d
出典データセット
uspto-grants-2016_09
特許番号
US09434718B2

関連ノート

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