Hydrochloric Acid → 2-Biphenyl-3-yl-4-methylpent-4-enoic acid

HRID 1060736

反応式

HRID 1060736 の反応式
[Li+].CC([N-]C(C)C)C.[C:9]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:10]=1.Br[CH2:26][C:27]([CH3:29])=[CH2:28].Cl>C1COCC1.C(OCC)(=O)C>[C:9]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH2:28][C:27]([CH3:29])=[CH2:26])[C:16]([OH:18])=[O:17])[CH:10]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 321533-Biphenylylacetic acidHCID 3577853-Bromo-2-methyl-1-propeneHCID 2724682Lithium diisopropylamide

生成物 1

HCID 218997992-Biphenyl-3-yl-4-methylpent-4-enoic acid収率 93%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

A solution of LDA (2.2 mL, 2.0 M in THF) in THF (20 mL) was cooled to 0° C. and then treated with biphenyl-3-ylacetic acid (0.212 g, 1.0 mmol). The mixture was stirred for 40 minutes, cooled to −78° C. and then treated with 3-bromo-2-methylpropene (135 μL, 1.3 mmol). The mixture was stirred for 1 hour, treated with 1 M hydrochloric acid (5 mL) and then diluted with ethyl acetate (50 mL). The organic layer was separated washed with water, brine, dried (MgSO4) and concentrated. Product was purified from the residue by flash column on silica gel (60° A) with 33% ethyl acetate in hexane to provide 2-biphenyl-3-yl-4-methylpent-4-enoic acid (250 mg, 0.93 mmol). 1H NMR (DMSO-d6): 1.71 (s, 3H), 2.52 (m, 2H), 3.68 (dd, 1H), 4.75 (m, 2H), 7.08 (d, 1H), 7.28-7.37 (m, 8H). LCMS: 267.1 (M+H+).

後処理

  1. stirringThe mixture was stirred for 1 hour
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customProduct was purified from the residue by flash column on silica gel (60° A) with 33% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-89201b9873bf45019bed15b90d7f7985
出典データセット
uspto-grants-2003_02
特許番号
US06525036B2

関連ノート

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