Boron trifluoride etherate → 6-[2-(5-Ethoxycarbonyl-5-methyl-hexyl)-[1,3]dithian-2-yl)-2,2-dimethyl-hexanoic acid ethyl ester

HRID 48001

반응식

HRID 48001 반응식
[CH2:1]([O:3][C:4](=[O:26])[C:5]([CH3:25])([CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:2].[CH2:27]([SH:31])[CH2:28][CH2:29][SH:30].B(F)(F)F.CCOCC>ClCCl>[CH2:1]([O:3][C:4](=[O:26])[C:5]([CH3:25])([CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:22])[CH3:21])[S:31][CH2:27][CH2:28][CH2:29][S:30]1)[CH3:2]

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 80131,3-PropanedithiolHCID 117266597-Oxo-2,2,12,12-tetramethyltridecanedioic acid diethyl ester

생성물 1

HCID 206312146-[2-(5-Ethoxycarbonyl-5-methyl-hexyl)-[1,3]dithian-2-yl)-2,2-dimethyl-hexanoic acid ethyl ester수율 80.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Under N2 atmosphere, to a solution of 2,2,12,12-tetramethyl-7-oxo-tridecanedioic acid diethyl ester (1.0 g, 2.70 mmol) and 1,3-propanedithiol (361 mg, 361 μL, 3.24 mmol) in dichloromethane (20 mL; dried with Aluminum oxide, activated, neutral, Brockmann I) was added boron trifluoride diethyl etherate (100 μL) at rt. The reaction mixture was stirred for 3 h, diluted with dichloromethane (100 mL), and extracted with 5% NaOH solution (100 mL) and water (75 mL). The organic phase was dried over MgSO4, concentrated in vacuo, and dried in high vacuo to furnish 6-[2-(5-ethoxycarbonyl-5-methyl-hexyl)-[1,3]dithian-2-yl]-2,2-dimethyl-hexanoic acid ethyl ester (1.0 g, 80%) as a yellowish oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 4.11 (q, 4H, J=7.1), 2.79 (t, 4H, J=5.6), 1.94 (m, 2H), 1.84 (m, 4H), 1.54 (m, 4H), 1.39 (m, 4H), 1.24 (t, 6H, J=7.1), 1.30-1.20 (m, 4H), 1.16 (s, 12H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 178.08, 60.33, 53.32, 42.27,40.69, 38.28, 26.14, 25.67, 25.28, 24.71, 14.41. HRMS (LSIMS, nba): Calcd. for C24H45S2O4 (MH+): 461.2759, found 461.2774.

후처리

  1. extractionextracted with 5% NaOH solution (100 mL) and water (75 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customdried in high vacuo

출처 및 근거

ORD 기록
ord-72112f38218540238068e9663f779046
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699910B2

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