Water → HCID 67072583、化合物

HRID 1948147ノート

反応式

HRID 1948147 の反応式
[CH:1]1([CH2:4][C:5]2([CH:15]=O)[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[CH3:17][C:18]([S:21]([NH2:23])=[O:22])([CH3:20])[CH3:19].O>O1CCCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH:1]1([CH2:4][C:5]2([CH:15]=[N:23][S:21]([C:18]([CH3:20])([CH3:19])[CH3:17])=[O:22])[CH2:6][CH2:7][C:8]3([O:9][CH2:10][CH2:11][O:12]3)[CH2:13][CH2:14]2)[CH2:2][CH2:3]1

参加物

6

反応物 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 866563378-Cyclopropylmethyl-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde

生成物 1

HCID 67072583HCID 67072583、化合物

試薬・触媒・溶媒 2

HCID 76524Titanium tetraethoxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

The crude aldehyde was dissolved in tetrahydrofuran (40 mL) and 2-methyl-2-propanesulfinamide (1.81 g, 14.9 mmol, 1.1 eq.) and titanium(IV) ethoxide (4.27 mL, 20.3 mmol, 1.5 eq.) were added. The resulting mixture was stirred for 5 h under reflux and 16 h at room temperature, before being treated with water (10 mL) and filtered through celite. The filter cake was washed with ethyl acetate, the aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulphate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane) to yield 1.90 g of the title compound (19). Rt=1.58 min (Method B). Detected mass: 328.3 (M+H+).

後処理

  1. filtrationfiltered through celite
  2. washThe filter cake was washed with ethyl acetate
  3. customthe aqueous layer was separated
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (SiO2, 0%→100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-909d78b107ad44cbb988c506077796e1
出典データセット
uspto-grants-2013_03
特許番号
US08399482B2

反応ノート

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