Hydrochloric Acid → HCID 57557635、化合物

HRID 2237767ノート

反応式

HRID 2237767 の反応式
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:13][C:14]1[CH:15]=[C:16]([C:24](OC)=[O:25])[C:17]([C:20](OC)=[O:21])=[CH:18][CH:19]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl>C1COCC1>[F:13][C:14]1[CH:15]=[C:16]2[C:17](=[CH:18][CH:19]=1)[C:20]([OH:21])=[C:2]([C:1]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:24]2[OH:25]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 31249Diethyl SuccinateHCID 2733832Lithium HexamethyldisilazideHCID 22744505Dimethyl 4-fluorobenzene-1,2-dicarboxylate

生成物 1

HCID 57557635HCID 57557635、化合物収率 28.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diethyl succinate (16.26 ml, 98.1 mmol) was added to dimethyl 4-fluoro-1,2-benzenedicarboxylate (10.4 g, 49.1 mmol) and LHMDS (1M in THF, 196 ml, 196 mmol) in THF (150 ml) at 10° C. (internal) over 30 minutes. Allowed to warm to room temperature slowly. After 20 hours, 2M HCl (˜500 ml) was added to acidify to pH 5. The mixture was extracted with EtOAc, then the organics washed with water, brine, dried over magnesium sulphate and concentrated in vacuo to give a brown oil. This was purified by chromatography on silica gel eluting with EtOAc/hexane (2:98) to yield the title compound as a yellow solid (4.58 g, 14.2 mmol).

後処理

  1. extractionThe mixture was extracted with EtOAc
  2. washthe organics washed with water, brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customto give a brown oil
  6. customThis was purified by chromatography on silica gel eluting with EtOAc/hexane (2:98)

出典と根拠

ORDレコード
ord-4e841ba7bd894b97acd86997aa3790ff
出典データセット
uspto-grants-2010_05
特許番号
US07718689B2

反応ノート

読み込み中…