Methyl iodide → Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate

HRID 511519

反応式

HRID 511519 の反応式
[Li+].[CH3:2]C([N-]C(C)C)C.[CH2:9]([O:11][C:12]([CH:14]1[CH2:23][CH2:22][C:17]2([O:21][CH2:20][CH2:19][O:18]2)[CH2:16][CH2:15]1)=[O:13])[CH3:10].CI>C1COCC1>[CH2:9]([O:11][C:12]([C:14]1([CH3:2])[CH2:23][CH2:22][C:17]2([O:18][CH2:19][CH2:20][O:21]2)[CH2:16][CH2:15]1)=[O:13])[CH3:10]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate2 回

生成物 1

HCID 19004805Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of LDA (7.0 mL, 14 mmol, 2M solution in THF/ethylbenzene) in THF (10 mL) was added a solution of 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (Compound 282H, 2.14 g, 9.99 mmol) in THF (5 mL) at −78° C. under nitrogen. The resulting mixture was stirred at this temperature for 30 min, then a solution of methyl iodide (1.98 g, 14.0 mmol) in THF (5 mL) was added. The resulting mixture was slowly warmed to rt overnight. The reaction was quenched with sat. aq. NH4Cl (20 mL) and diluted with EtOAc (50 mL). The organic layer was washed with brine (30 mL), and dried over anhydrous sodium sulfate. The solvents were evaporated under reduced pressure to give the desired compound as a light-yellow oil, 2.30 g, 100% yield. The material was used in next step without further purification. 1H NMR (CDCl3): 1.20 (s, 3H), 1.26 (t, J=7.1 Hz, 3H), 1.52-1.68 (m, 6H), 2.12-2.17 (m, 2H), 3.94 (s, 4H), 4.15 (q, J=7.1 Hz, 2H).

後処理

  1. customThe reaction was quenched with sat. aq. NH4Cl (20 mL)
  2. additiondiluted with EtOAc (50 mL)
  3. washThe organic layer was washed with brine (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvents were evaporated under reduced pressure

出典と根拠

ORDレコード
ord-5b988ca115bf4d7b8db743b2e7160ae8
出典データセット
uspto-grants-2015_08
特許番号
US09096624B2

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