Sodium Thiosulfate → HCID 178501146, 화합물

HRID 1482886노트

반응식

HRID 1482886 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([C:31]([O:33][CH3:34])=[O:32])[CH2:27][CH2:26]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1>[CH:24]([C@H:25]1[CH2:26][CH2:27][C@H:28]([C:31]([O:33][CH3:34])=[O:32])[CH2:29][CH2:30]1)=[O:23]

참가 물질

5

반응물 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 178501147HCID 178501147, 화합물

생성물 1

HCID 178501146HCID 178501146, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of Dess-Martin periodinane (542 mg, 1.28 mmol) in THF (2 mL) was added methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (200 mg, 1.18 mmol) at 0° C., and the reaction mixture was then stirred at 20° C. for 3 hours before the addition of saturated aqueous sodium thiosulfate solution (50 mL). The mixture was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by prep-TLC (ethyl acetate/petroleum ether) to give methyl trans-4-formylcyclohexanecarboxylate. MS ESI calc'd. for C9H15O3[M+H]+ 171. found 171. 1H NMR: (400 MHz, CDCl3) δ 9.63 (s, 1H), 3.68 (s, 3H), 2.36-2.17 (m, 2H), 2.13-2.04 (m, 4H), 1.55-1.45 (m, 2H), 1.37-1.25 (m, 2H).

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep-TLC (ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-ef55d95d3bfb4379bb406ffd8f2ec36c
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416111B2

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