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

HRID 511519

반응식

HRID 511519 반응식
[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]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5b988ca115bf4d7b8db743b2e7160ae8
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096624B2

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