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

HRID 357882ノート

反応式

HRID 357882 の反応式
[OH:1][C:2]1[CH2:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[O:5][C:4](=[O:19])[CH:3]=1.CCN(CC)CC.[CH3:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](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]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[O:5][C:4](=[O:19])[C:3]=1[CH2:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:30]([CH3:31])[CH:29]=1

参加物

9

反応物 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2 回HCID 743753-Methylbenzoyl chlorideHCID 5003444Sodium cyanoborohydrideHCID 546907045,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

生成物 1

HCID 547216225,6-Dihydro-4-hydroxy-6-(3-methylbutyl)-3-[(3-methylphenyl)methyl]-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-phenyl-6-(3-methylbutyl)-2H-pyran-2-one (0.300 g, 1.15 mmol), Et3N (0.17 mL, 1.2 mmol), 3-methylbenzoyl chloride (0.15 mL, 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 (4.0 mL), sodium cyanoborohydride (0.51 g, 8.1 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 0.5% MeOH in CH2Cl2) to provide a solid (0.252 g, 53°-55° C.). 1H NMR (400 MHz, DMSO-d6) δ 7.376-7.244 (m, 5 H), 6.915 (t, 1 H, J=7.5 Hz), 6.831 (d, 1 H, J=7.5 Hz), 6.549 (d, 1 H, J=7.5 Hz), 6.509 (s, 1 H), 3.369 (AB, 2 H, JAB =14.4 Hz), 3.112 (AB, 2 H, JAB =17.5 Hz), 2.088 (s, 3 H), 1.962 (m, 2 H), 1.416-1.333 (m, 1 H), 1.152-1.061 (m, 1 H), 0.898-0.726 (m, 7 H).

後処理

  1. customPurification
  2. customto provide a solid (0.252 g, 53°-55° C.)

出典と根拠

ORDレコード
ord-eba171c9b7bc4fb89265d025d0ff42f0
出典データセット
uspto-grants-1998_11
特許番号
US05840751

反応ノート

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