Dichloromethane → HCID 86705754、化合物

HRID 1054540ノート

反応式

HRID 1054540 の反応式
[Cl:1][C:2]1[C:3](C(F)(F)F)=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[N:7]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:6]=2[CH:23]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(Cl)[Cl:51]>>[Cl:51][C:3]1[C:2]([Cl:1])=[CH:23][C:6]2[N:7]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]([CH2:10][CH2:11][CH2:12][CH:13]=[O:14])=[N:9][C:5]=2[CH:4]=1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 67818597HCID 67818597、化合物

生成物 1

HCID 86705754HCID 86705754、化合物

実験手順

4-[6-chloro-5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]butan-1-ol (1.00 g, 2.36 mmol) was dissolved in DCM (30 ml) and Dess-Martin reagent (1.10 g, 2.60 mmol) was added at r.t. The reaction was left for 4 hrs. The reaction was quenched by the addition of 1M Na2S2O3 solution (10 ml), sat. NaHCO3 solution (40 ml) and DCM (80 ml). The organic layer was separated and the aqueous layer was extracted with DCM (3×80 ml). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product. The product was purified by silica flash column chromatography eluting with EtOAc:heptanes (1:1) as a light orange oil (0.53 g, 38%): MS (ESI+) for C18H24ClF3N2O2Si m/z 422.05 [M+H]+; LC purity 72% (ret. time, 1.81 min); 1H NMR (250 MHz, CHLOROFORM-d) δ ppm −0.21-0.21 (9H, m), 0.77-1.01 (2H, m), 2.17-2.36 (2H, m), 2.64-2.86 (2H, m), 3.02 (2H, td, J=7.39, 3.20 Hz), 3.35-3.74 (2H, m), 5.39-5.60 (2H, m), 7.34-8.18 (2H, m), 9.82 (1H, s).

後処理

  1. customThe reaction was quenched by the addition of 1M Na2S2O3 solution (10 ml), sat. NaHCO3 solution (40 ml) and DCM (80 ml)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (3×80 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-841bb0245a70470a98a20d85938773f5
出典データセット
uspto-grants-2016_07
特許番号
US09394310B2

反応ノート

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