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

HRID 1585425노트

반응식

HRID 1585425 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 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).

후처리

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

출처 및 근거

ORD 기록
ord-10490d13c34e431e820ad70858362839
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05936128

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