Diisopropylamine → 4-Tert-butyl-2-(carboxymethyl)benzoic acid

HRID 2236489ノート

反応式

HRID 2236489 の反応式
C(NC(C)C)(C)C.[Li]CCCC.[C:13]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[C:19]([CH3:26])[CH:18]=1)([CH3:16])([CH3:15])[CH3:14].C[O:28][C:29](=O)[O:30]C>C1COCC1>[C:13]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[C:19]([CH2:26][C:29]([OH:30])=[O:28])[CH:18]=1)([CH3:16])([CH3:15])[CH3:14]

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 12021Dimethyl CarbonateHCID 119589774-Tert-butyl-2-methylbenzoic acidHCID 178418339Butyllithium

生成物 1

HCID 426258304-Tert-butyl-2-(carboxymethyl)benzoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a magnetically stirred solution of diisopropyl amine (0.75 g, 7.4 mmol) in THF (5 mL) at −30° C. is added BuLi (3.4 mL, 2.5 M in hexanes, 8.5 mmol). The mixture is stirred for 10 minutes at this temperature and cooled to −78° C. A solution of 4-tert-Butyl-2-methyl-benzoic acid [J. Am. Chem. Soc. 1944, 66, 154] (250 mg, 1.3 mmol) and dimethylcarbonate (150 mg, 1.67 mmol) in THF (3 mL) is added dropwise at −78° C. The mixture is allowed to stir at this temperature for 2 hours before it is allowed to warm to room temperature. The mixture is quenched with MeOH and water once it reached room temperature. After removal of THF, the water layer is extracted with ether. The water layer is acidified with HCl and the product is extracted from ether. After chromatography, the title compound is isolated pure (125 mg, 41%). MS (ESI): 237.1 (M+1)+1.

後処理

  1. stirringto stir at this temperature for 2 hours before it
  2. temperatureto warm to room temperature
  3. customThe mixture is quenched with MeOH and water once it
  4. customreached room temperature
  5. customAfter removal of THF
  6. extractionthe water layer is extracted with ether
  7. extractionthe product is extracted from ether

出典と根拠

ORDレコード
ord-f601c3286c17427caa1a2505a2a7ef38
出典データセット
uspto-grants-2010_05
特許番号
US07713994B2

反応ノート

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