Tetrahydrofuran → HCID 86702582, 화합물

HRID 1746815노트

반응식

HRID 1746815 반응식
[O:1]1CC[CH2:3][CH2:2]1.[CH3:6][Si:7]([CH3:37])([C:33]([CH3:36])([CH3:35])[CH3:34])[O:8][CH2:9][C@H:10]1[C@H:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13][C@H:12]([OH:22])[C@@H:11]1[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>C(OCC)(=O)C.CCCCCC.O.C(O)(=O)C>[C:2]([O:22][C@H:12]1[C@H:11]([CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C@@H:10]([CH2:9][O:8][Si:7]([CH3:6])([CH3:37])[C:33]([CH3:34])([CH3:36])[CH3:35])[C@H:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13]1)(=[O:1])[CH3:3]

참가 물질

9

반응물 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 13080739HCID 13080739, 화합물HCID 66777355Diethylazodicarboxylate toluene

생성물 1

HCID 86702582HCID 86702582, 화합물

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 962Water용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

An anhydrous tetrahydrofuran (482 mL) solution of the compound 3 (79.6 g) and triphenylphosphine (57.6 g) was cooled to around −40° C. in a dry ice-methanol bath. To this solution was added acetic acid (12.6 mL), and a 40% diethyl azodicarboxylate/toluene solution (100 mL) was then added dropwise over 15 minutes. The mixture was stirred at room temperature for 4.5 hours, the reaction mixture was then poured into water (1600 mL), a mixed solution of hexane (550 mL) and ethyl acetate (550 mL) was added, and the mixture was stirred. The two layers were separated, and the organic layer was then washed with water (540 mL) and a saturated saline (540 mL), dried with anhydrous sodium sulfate, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain a titled compound (69.7 g) having the following physical property values.

후처리

  1. stirringthe mixture was stirred
  2. customThe two layers were separated
  3. washthe organic layer was then washed with water (540 mL)
  4. dry with materiala saturated saline (540 mL), dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-891ca50e8aca404987e596f5c2729b41
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150537B2

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