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丙酮氰醇 → 4-hydroxy-2-phenethyl-2-phenyl-5-[[2-(trifluoromethyl)phenyl]methyl]-3H-pyran-6-one

HRID 481908
笔记
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反应方程式

HRID 481908 反应方程式
[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]
参与物实验过程后处理来源与证据反应笔记

参与物

9

反应物 5

HCID 6406丙酮氰醇HCID 8471三乙胺2 次HCID 675612-三氟甲基苯甲酰氯HCID 5003444氰基硼氢化钠HCID 546823015,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

产物 1

HCID 547140754-hydroxy-2-phenethyl-2-phenyl-5-[[2-(trifluoromethyl)phenyl]methyl]-3H-pyran-6-one

试剂、催化剂与溶剂

3
HCID 176醋酸溶剂HCID 6342乙腈溶剂HCID 6344二氯甲烷溶剂

实验过程

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) δ11.21 (bs, 1H), 7.584 (d, 1H, J=8 Hz), 7.457-7.030 (m, 12H), 6.179 (d, 1H, J=7.5 Hz), 3.594 (s, 2H), 3.362 (d, 1H, J=17 Hz), 3.249 (d, 1H, J=17 Hz), 2.686-2.603 (m, 1H), 2.374-2.182 (m, 3H).

后处理

  1. customPurification

来源与证据

ORD记录
ord-a3151f91d52944cea4e31f96fae817f1
来源数据集
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
专利号
US05789440

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记