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1,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate → 8-(5-Isopropoxy-2-methyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

HRID 386792
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HRID 386792 반응식
FC(F)(F)S(O[C:7]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH:8]=1)(=O)=O.[CH:19]([O:22][C:23]1[C:24]([N+:39]([O-:41])=[O:40])=[CH:25][C:26]([CH3:38])=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:28]=1)([CH3:21])[CH3:20].[O-]P([O-])([O-])=O.[K+].[K+].[K+].O.CCCCCC.CCOC(C)=O>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]([O:22][C:23]1[C:24]([N+:39]([O-:41])=[O:40])=[CH:25][C:26]([CH3:38])=[C:27]([C:7]2[CH2:16][CH2:15][C:10]3([O:14][CH2:13][CH2:12][O:11]3)[CH2:9][CH:8]=2)[CH:28]=1)([CH3:21])[CH3:20]
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참가 물질

7

반응물 4

HCID 114830861,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonateHCID 21226206Ethyl acetate hexaneHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 597645312-(5-Isopropoxy-2-methyl-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane2회

생성물 1

HCID 597645528-(5-Isopropoxy-2-methyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

A stirred solution of the 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (0.03 mmol) and 2-(5-isopropoxy-2-methyl-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Intermediate 5, 0.04 mmol) in THF (3 mL), containing [Pd(PPh3)4] (0.013 mmol) and K3PO4.H2O (0.045 mmol), is heated to 80° C. under argon for 16 hours. After workup and silica flash chromatography (hexane/EtOAc 4:1), 8-(5-isopropoxy-2-methyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene is obtained. 1H NMR (CDCl3, 400 MHz) δ 7.62 (s, 1H), 6.82 (s, 1H), 5.74 (m, 1H), 4.65 (m, 1H), 4.04 (m. 4H), 2.47 (m, 4H), 2.27 (s, 3H), 1.89 (t, 2H), 1.29 (d. 6H). MS (ES+): 334.16 (M+1)+.

출처 및 근거

ORD 기록
ord-9f5a138b88824988a74065f289dba871
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08372858B2

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