Triphenylphosphine → (3-(4-((1,3-Dioxolan-2-yl)methyl)benzyloxy)phenyl)-(phenyl)methanone

HRID 332655

反応式

HRID 332655 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1.O[C:16]1[CH:17]=[C:18]([CH:27]=[CH:28][CH:29]=1)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(OCC)(=O)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:25]2[CH:26]=[C:21]([C:19]([C:18]3[CH:27]=[CH:28][CH:29]=[CH:16][CH:17]=3)=[O:20])[CH:22]=[CH:23][CH:24]=2)=[CH:9][CH:8]=1

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 830503-HydroxybenzophenoneHCID 86676898(4-((1,3-Dioxolan-2-yl)methyl)phenyl)methanol

生成物 1

HCID 71113108(3-(4-((1,3-Dioxolan-2-yl)methyl)benzyloxy)phenyl)-(phenyl)methanone収率 117.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a cooled (0° C.) solution of (4-((1,3-dioxolan-2-yl)methyl)phenyl)methanol (0.45 g, 2.317 mmol), 3-hydroxybenzophenone (0.551 g, 2.78 mmol) and triphenylphosphine (0.729 g, 2.78 mmol) in anhydrous THF, di-iso-propylazodicarboxylate (1.027 mL, 2.78 mmol) was added dropwise. The reaction mixture was allowed to warm to RT and stirred at this temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with 10% aqueous potassium carbonate, brine and dried (magnesium sulfate). The suspension was filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 100% iso-hexane to 25% ethyl acetate in iso-hexane to afford the title compound (1.022 g, >100%).

後処理

  1. additionwas added dropwise
  2. washwashed with 10% aqueous potassium carbonate, brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationThe suspension was filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with 100% iso-hexane to 25% ethyl acetate in iso-hexane

出典と根拠

ORDレコード
ord-25d0f516749b4f2e97a0a4f49ecfd867
出典データセット
uspto-grants-2014_11
特許番号
US08877774B2

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