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

HRID 1585425ノート

反応式

HRID 1585425 の反応式
[OH:1][C:2]1[CH2:7][C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:20])[CH:3]=1.CCN(CC)CC.[CH:28]([C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](Cl)=O)([CH3:30])[CH3:29].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:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:5][C:4](=[O:20])[C:3]=1[CH2:33][C:32]1[CH:36]=[CH:37][CH:38]=[CH:39][C:31]=1[CH:28]([CH3:30])[CH3:29]

参加物

9

反応物 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2 回HCID 5003444Sodium cyanoborohydrideHCID 212225852-Isopropylbenzoyl chlorideHCID 546804105,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

生成物 1

HCID 547216355,6-Dihydro-4-hydroxy-3-[(2-isopropylphenyl)methyl]-6,6-diphenyl-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-6,6-diphenyl-2H-pyran-2-one (0.300 g, 1.15 mmol), Et3N (0.17 mL, 1.2 mmol), 2-isopropylbenzoyl chloride (1.02 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, 8.5 mmol). Purification was achieved by submitting the final residue to column chromatograpy (SiO2, 100% CH2Cl2 to 1% MeOH in CH2Cl2) to provide a solid (0.128 g, 224-226° C.). 1H NMR (400 MHz, DMSO-d6) δ 11.180 (bs, 1 H), 7.445-7.235 (m, 10 H), 7.109 (d, 1 H, J=7.5 Hz), 6.970 (t, 1 H, J=7.5 Hz), 6.515 (t, 1 H, J=7.5 Hz), 5.841 (d, 1 H, J=7.5 Hz), 3.560 (s, 2 H), 3.463 (s, 2 H), 1.174-1.094 (m, 7 H).

後処理

  1. customPurification
  2. customto provide a solid (0.128 g, 224-226° C.)

出典と根拠

ORDレコード
ord-10490d13c34e431e820ad70858362839
出典データセット
uspto-grants-1999_08
特許番号
US05936128

反応ノート

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