Tetrahydrofuran → HCID 86702582、化合物

HRID 1746815ノート

反応式

HRID 1746815 の反応式
[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]

参加物

9

反応物 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 13080739HCID 13080739、化合物HCID 66777355Diethylazodicarboxylate toluene

生成物 1

HCID 86702582HCID 86702582、化合物

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-891ca50e8aca404987e596f5c2729b41
出典データセット
uspto-grants-2015_10
特許番号
US09150537B2

反応ノート

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