Sulfuric Acid → (R)-tert-Butyl 2-chloropropanoate

HRID 708398ノート

反応式

HRID 708398 の反応式
S([O-])([O-])(=O)=O.[Mg+2].S(=O)(=O)(O)O.[Cl:12][C@H:13]([CH3:17])[C:14]([OH:16])=[O:15].[C:18](O)([CH3:21])([CH3:20])[CH3:19].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:12][C@H:13]([CH3:17])[C:14]([O:16][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15]

参加物

7

反応物 5

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 27245402-Chloropropionic acid, (+)-

生成物 1

HCID 10986598(R)-tert-Butyl 2-chloropropanoate収率 94.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Prepared according to Wright et al. Tetrahedron Lett. 1997, 38, 7345. A 500 mL glass bomb was charged with magnesium sulfate (4.21 g, 35.0 mmol) and DCM (43.8 mL). To this suspension was added sulfuric acid (486 μL, 8.75 mmol), drop-wise with vigorous stirring. After 15 min of stirring, (R)-2-chloropropanoic acid (950 mg, 8.75 mmol) was added followed by tert-butanol (4.20 ml, 43.8 mmol). The bomb was sealed and stirred at rt for 19 h, whereupon sodium bicarbonate (aq satd, 100 mL) was carefully added, at which point all solids had dissolved. The layers were separated and the aqueous layer was extracted with DCM (2×). The combined organics layers were washed with brine, dried over Na2SO4 and concentrated in vacuo (20° C. bath, 50 mBar) to afford the title compound (1.36 g, 94%) as a light pink oil. 1H NMR (500 MHz, CDCl3) δ 4.29 (q, J=6.9 Hz, 1H) 1.65 (d, J=6.9 Hz, 3H) 1.49 (s, 9H).

後処理

  1. customPrepared
  2. customThe bomb was sealed
  3. additionwas carefully added, at which point all solids
  4. dissolutionhad dissolved
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with DCM (2×)
  7. washThe combined organics layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo (20° C. bath, 50 mBar)

出典と根拠

ORDレコード
ord-4c78690346ff488f850b83ae9dcd16ba
出典データセット
uspto-grants-2015_11
特許番号
US09174978B2

反応ノート

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