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Acetone Cyanohydrin → 4-hydroxy-2-phenethyl-2-phenyl-5-[[2-(trifluoromethyl)phenyl]methyl]-3H-pyran-6-one

HRID 357880
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HRID 357880 반응식
[OH:1][C:2]1[CH2:7][C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:22])[CH:3]=1.CCN(CC)CC.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=1[C:34](Cl)=O.CC(C)(O)C#N.C([BH3-])#N.[Na+]>C(O)(=O)C.C(#N)C.C(Cl)Cl>[OH:1][C:2]1[CH2:7][C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:22])[C:3]=1[CH2:34][C:33]1[CH:37]=[CH:38][CH:39]=[CH:40][C:32]=1[C:31]([F:30])([F:41])[F:42]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2회HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546823015,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

생성물 1

HCID 54714075
4-hydroxy-2-phenethyl-2-phenyl-5-[[2-(trifluoromethyl)phenyl]methyl]-3H-pyran-6-one

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared as described in General Method 8 using the following: 5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (0.300 g, 1.02 mmol), Et3N (0.15 mL, 1.1 mmol), 2-trifluoromethylbenzoyl chloride (0.21 mL, 1.02 mmol), CH2Cl2 (4.0 mL), acetonitrile (4.0 mL), acetone cyanohydrin (0.04 mL, 0.47 mmol), Et3N (0.29 mL, 2,1 mmol), glacial acetic acid (3.0 mL), sodium cyanoborohydride (0.20 g, 3.1 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 1% MeOH in CH2Cl2) to provide an oil (0.102 g). 1H NMR (400 MHz, DMSO-d6) δ 11.21 (bs, 1 H), 7.584 (d, 1 H, J=8 Hz), 7.457-7.030 (m, 12 H), 6.179 (d, 1 H, J=7.5 Hz), 3.594 (s, 2 H), 3.362 (d, 1 H, J=17 Hz), 3.249 (d, 1 H, J=17 Hz), 2.686-2.603 (m, 1 H), 2.374-2.182 (m, 3 H).

후처리

  1. customPurification

출처 및 근거

ORD 기록
ord-c028fca2564c4d14b2416c2ca931383c
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05840751

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