Sodium Hydroxide → 6-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

HRID 1003839노트

반응식

HRID 1003839 반응식
C[O:2][C:3](=[O:25])[CH2:4][C:5](=[O:24])[CH2:6][C:7]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)(O)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.[OH-].[Na+]>O1CCCC1>[CH:18]1([C:7]2([CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)[O:25][C:3](=[O:2])[CH:4]=[C:5]([OH:24])[CH2:6]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 543367345-Cyclohexyl-5-hydroxy-7-(4-hydroxy-phenyl)-3-oxo-heptanoic acid methyl ester

생성물 1

HCID 547203146-Cyclohexyl-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Crude 5-cyclohexyl-5-hydroxy-7-(4-hydroxy-phenyl)-3-oxo-heptanoic acid methyl ester (prepared in the previous paragraph) was dissolved in tetrahydrofuran (100 mL) and treated with 0.2N NaOH (900 mL) as described in General Method 7. The reaction was stirred for 3 hours at room temperature and then worked up as usual. The organic extracts obtained were combined, dried (MgSO4) and concentrated. Purification was accomplished by flash chromatography using CH2Cl2 :MeOH (99:1 to 98:2) to give the desired product as a solid, m.p. 52-58° C. 1H NMR (CDCl3) δ 1.0-1.9 (m, 12 H), 1.9-2.1 (m, 1 H), 2.5-2.7 (m, 3 H), 2.8 (d, 1 H), 3.4 (s, 2 H), 6.75 (d, 2 H), 7.05 (d, 2 H).

후처리

  1. customThe organic extracts obtained
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customPurification

출처 및 근거

ORD 기록
ord-d42bb242e0ac49eb94623f57e2788d76
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046355

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