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Triethylamine → 2-(4,5-Diphenyloxazol-2-yl)-3-(3-t-butyldiphenylsilyloxybenzyl)tetrahydrothiophene

HRID 380090
ノート
印刷プレビュー

反応式

HRID 380090 の反応式
[C:1]1([C:7]2[N:8]=[C:9]([CH:18](O)[CH:19]([CH2:45][CH2:46]O)[CH2:20][C:21]3[CH:22]=[C:23]([O:27][Si:28]([C:41]([CH3:44])([CH3:43])[CH3:42])([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:24]=[CH:25][CH:26]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[S:50](Cl)(=O)=O.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH:19]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][Si:28]([C:41]([CH3:44])([CH3:43])[CH3:42])([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH:22]=4)[CH2:45][CH2:46][S:50]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 183674053-[3-(4,5-Diphenyloxazol-2-yl)-3-hydroxy-2-(2-hydroxyethyl)propyl]-1-(t-butyldiphenylsilyloxy)benzene

生成物 1

HCID 183674322-(4,5-Diphenyloxazol-2-yl)-3-(3-t-butyldiphenylsilyloxybenzyl)tetrahydrothiophene

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-[3-(4,5-diphenyloxazol-2-yl)-3-hydroxy-2-(2-hydroxyethyl)propyl]-1-(t-butyldiphenylsilyloxy)benzene (3.0 g) and methanesulfonyl chloride (1.1 ml) and triethylamine (2.6 ml) in THF (50 ml) was stirred at room temperature for 1 hour. The solution was diluted with ethyl acetate and washed with sat. NaHCO3 and brine, dried over MgSO4, and evaporated. The residue was dissolved in DMF (40 ml) and to the solution was added Na2S (600 mg). After being stirred for 30 minutes at 80° C., the mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, sat. NaHCO3, and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to afford 2-(4,5-diphenyloxazol-2-yl)-3-(3-t-butyldiphenylsilyloxybenzyl)tetrahydrothiophene (3.2 g).

後処理

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. dissolutionThe residue was dissolved in DMF (40 ml) and to the solution
  5. additionwas added Na2S (600 mg)
  6. stirringAfter being stirred for 30 minutes at 80° C.
  7. customthe mixture was partitioned between ethyl acetate and water
  8. washThe organic layer was washed with water, sat. NaHCO3, and brine
  9. customThe dried solvent was evaporated in vacuo
  10. customthe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-03ca475a056a46b1a1f88af84315f0d4
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06300344B1

反応ノート

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