1,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate → HCID 70819584, compound

HRID 591061Notes

Reaction equation

HRID 591061 reaction equation
[C:1]([O:5][CH:6]([C:12]1[C:16](B2OC(C)(C)C(C)(C)O2)=[C:15]([CH3:26])[S:14][C:13]=1[CH3:27])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)S(OC1CCC2(OCCO2)CC=1)(=O)=O.C(OC(C1[C:61]([C:62]2[CH2:71][CH2:70][C:65]3(OCCO3)[CH2:64][CH:63]=2)=C(C)SC=1C)C(OCC)=O)(C)(C)C>>[C:1]([O:5][CH:6]([C:12]1[C:16]([C:61]2[CH2:62][CH2:71][CH2:70][CH2:65][CH2:64][CH:63]=2)=[C:15]([CH3:26])[S:14][C:13]=1[CH3:27])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 114830861,4-Dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonateHCID 70818507HCID 70818507, compoundHCID 70819500HCID 70819500, compound

Product 1

HCID 70819584HCID 70819584, compound

Procedure

Using the procedure described in example 29, step 2, ethyl 2-(tert-butoxy)-2-[2,5-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl]acetate (28f) (100 mg, 0,246 mmol) is converted, by reaction with 1,4-dioxaspiro[4.5]dec-7-en-8-yl trifluoromethanesulfonate (34a) and after purification by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10), to ethyl 2-(tert-butoxy)-2-(4-{1,4-dioxaspiro[4.5]dec-7-en-8-yl}-2,5-dimethylthiophen-3-yl)acetate (34b) (39 mg, 0.10 mmol, 39%).

Workup

  1. customafter purification by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-eaf6bf3dcab0489283ae8100516ed759
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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