2,6-Lutidine → (S)-4-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)benzonitrile

HRID 1948495ノート

反応式

HRID 1948495 の反応式
[Br:1][CH2:2][C@H:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)[OH:4].CC1C=CC=C(C)N=1.[Si:21](OS(C(F)(F)F)(=O)=O)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][CH2:2][C@H:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)[O:4][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

参加物

6

反応物 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 66955119(S)-4-(2-bromo-1-hydroxyethyl)benzonitrile

生成物 1

HCID 66955431(S)-4-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)benzonitrile収率 115.6%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of (S)-4-(2-bromo-1-hydroxyethyl)benzonitrile (6.9 g, 30.5 mmol) and 2,6-dimethylpyridine (7.82 mL, 67.1 mmol) in DCM (20 mL) was added t-butyl-dimethylsilyltrifluoromethanesulfonate (14.02 mL, 61.0 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with saturated NaCl. The organic layer was dried MgSO4, filtered and concentrated. The crude material was purified on a 80 gram silica column and eluting with an EtOAc/Hex gradient to afford 12 g of (S)-4-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)benzonitrile. MS (M+1)=340/342. HPLC Peak RT=2.16 minutes. 1H NMR (400 MHz, CDCl3) δ ppm 7.65 (2H, d), 7.45 (2H, d), 4.88 (1H, dd), 3.42 (1H, q), 3.39 (1H, dd), 0.85 (9H, s), 0.12 (3H, s), −0.09 (3H, s).

後処理

  1. washwashed with saturated NaCl
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude material was purified on a 80 gram silica column
  5. washeluting with an EtOAc/Hex gradient

出典と根拠

ORDレコード
ord-8abf08f4b5074a09b24362d3ebe14aa7
出典データセット
uspto-grants-2013_03
特許番号
US08399451B2

反応ノート

読み込み中…