Acetone Cyanohydrin → 5,6-Dihydro-4-hydroxy-3-[(2-isopropylphenyl)methyl]-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

HRID 481915ノート

反応式

HRID 481915 の反応式
[OH:1][C:2]1[CH2:7][C:6]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:19])[CH:3]=1.CCN(CC)CC.[CH:27]([C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=O)([CH3:29])[CH3:28].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]([CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:5][C:4](=[O:19])[C:3]=1[CH2:32][C:31]1[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=1[CH:27]([CH3:29])[CH3:28]

参加物

9

反応物 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2 回HCID 5003444Sodium cyanoborohydrideHCID 212225852-Isopropylbenzoyl chlorideHCID 546907045,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

生成物 1

HCID 547217485,6-Dihydro-4-hydroxy-3-[(2-isopropylphenyl)methyl]-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

The title compound was prepared as described in General Method 8 using the following: 5,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one (0.300 g, 1.15 mmol), Et3N (0.17 mL, 1.2 mmol), 2-isopropylbenzoyl chloride (1.15 mmol), CH2Cl2 (4.0 mL), acetonitrile (4.0 mL), acetone cyanohydrin (0.05 mL, 0.5 mmol), Et3N (0.35 mL, 2.5 mmol), glacial acetic acid (5.0 mL), sodium cyanoborohydride (0.50 g, 8.1 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2) to provide a solid (0.118 g, 124°-126° C.). 1H NMR (400 MHz, DMSO-d6) δ10.855 (bs, 1H), 7.395-7.306 (m, 5H), 7.115 (dd, 1H, J=1 Hz, J=7.5 Hz), 6.991 (t, 1H, J=7 Hz), 6.622 (td, 1H, J=1 Hz, J=7 Hz), 6.123 (d, 1H, J=7 Hz), 3.422 (s, 2H), 3.210-3.102 (m, 3H), 1.975-1.871 (m, 2H), 1.437-1.371 (m, 1H), 1.142-1.084 (m, 7H), 0.938-0.807 (m, 1H), 0.791-0.766 (m, 6H).

後処理

  1. customPurification
  2. customto provide a solid (0.118 g, 124°-126° C.)

出典と根拠

ORDレコード
ord-dbd978f38e0d4e478fcacd7f5951f364
出典データセット
uspto-grants-1998_08
特許番号
US05789440

反応ノート

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