乙醚 → rel-Methyl (1R,2S)-3-oxo-2-pentylcyclopentaneacetate

HRID 2377

反应方程式

HRID 2377 反应方程式
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([CH2:7][C:8]([OH:10])=[O:9])[C@H:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH3:16]OS(OC)(=O)=O.CCOCC>CC(C)=O.O>[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([CH2:7][C:8]([O:10][CH3:16])=[O:9])[C@H:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

参与物

6

反应物 3

HCID 3283乙醚HCID 6497甲基硫酸酯-13C2HCID 16061083(1S,2R)-3-oxo-2-pentyl-cyclopentaneacetic acid

产物 1

HCID 1738127rel-Methyl (1R,2S)-3-oxo-2-pentylcyclopentaneacetate收率 89.8%

试剂、催化剂与溶剂 2

HCID 180丙酮溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

To 104 mg (0.49 mmole) of (±)cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid (93:7 cis/trans ratio) in 1 ml of (CH3)2CO there were added, first 56 μl of (CH3)2SO4 (74 ml, 0.59 mmole, 1.2 eq.) and then 81 mg (0.59 mmole, 1.2 eq.) of anhydrous solid K2 CO3. The resulting suspension was heated at r.t. during 4 h and taken in water and with ether. The ether phase was separated and the aqueous phase once more extracted with ether. The combined organic phases were washed with water, dried over MgSO4, filtered and concentrated. The residue was distilled in a bulb-to-bulb apparatus (oven t.: 180°/7 Pa) to provide 93 mg (0.44 mmole, yield 84%) of methyl (±)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate (92/8 cis/trans ratio).

后处理

  1. customThe ether phase was separated
  2. extractionthe aqueous phase once more extracted with ether
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationThe residue was distilled in a bulb-to-bulb apparatus (oven t.: 180°/7 Pa)

来源与证据

ORD记录
ord-cb6326117e3045cb93e4c9a0471e9b58
来源数据集
uspto-grants-1998_03
专利号
US05728866

关联笔记

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