4-(Trifluoromethyl)-1-cyclohexen-1-yl 1,1,1-trifluoromethanesulfonate → HCID 70818742, compound

HRID 591064Notes

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(O[C:34]1[CH2:39][CH2:38][CH:37]([C:40]([F:43])([F:42])[F:41])[CH2:36][CH:35]=1)(=O)=O.C(OC(C1C(C2CCC(C(F)(F)F)CC=2)=C(C)SC=1C)C([O-])=O)(C)(C)C>>[C:1]([O:5][CH:6]([C:12]1[C:16]([C:34]2[CH2:39][CH2:38][CH:37]([C:40]([F:43])([F:42])[F:41])[CH2:36][CH:35]=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

Reactant 3

HCID 116018164-(Trifluoromethyl)-1-cyclohexen-1-yl 1,1,1-trifluoromethanesulfonate

HCID 70818507HCID 70818507, compound

HCID 131734507HCID 131734507, compound

Product 1

HCID 70818742HCID 70818742, 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) (60 mg, 0,148 mmol) is converted, by reaction with 4-(trifluoromethyl)cyclohex-1-en-1-yl trifluoromethanesulfonate (41a) and after purification by preparative TLC (cyclohexane/ethyl acetate 90/10), to 2-(tert-butoxy)-2-{2,5-dimethyl-4-[4-(trifluoromethyl)cyclohex-1-en-1-yl]thiophen-3-yl}acetate (41b) (31 mg, 0.07 mmol, 50%).

Workup

customafter purification by preparative TLC (cyclohexane/ethyl acetate 90/10)

Sources & evidence

ORD record: ord-517551ba70b044989d477526399a8e0c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238026B2

Reaction notes

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