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

HRID 481909노트

반응식

HRID 481909 반응식
[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]

참가 물질

9

반응물 5

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2회HCID 5003444Sodium cyanoborohydrideHCID 212225852-Isopropylbenzoyl chlorideHCID 546804105,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

생성물 1

HCID 547216355,6-Dihydro-4-hydroxy-3-[(2-isopropylphenyl)methyl]-6,6-diphenyl-2H-pyran-2-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-6,6-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 CH2 Cl2) to provide a solid (0.128 g, 224°-226° C.). 1H NMR (400 MHz, DMSO-d6) δ11.180 (bs, 1H), 7.445-7.235 (m, 10H), 7.109 (d, 1H, J=7.5 Hz), 6.970 (t, 1H, J=7.5 Hz), 6.515 (t, 1H, J=7.5 Hz), 5.841 (d, 1H, J=7.5 Hz), 3.560 (s, 2H), 3.463 (s, 2H), 1.174-1.094 (m, 7H).

후처리

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

출처 및 근거

ORD 기록
ord-7446ed9c48e24865a46ea6efe6d5729d
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789440

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