Potassium Hydroxide → HCID 59853673, compound

HRID 2374233Notes

Reaction equation

HRID 2374233 reaction equation
[C:1]1(B2OC(C)(C)C(C)(C)O2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.I[C:17]1[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][C:18]=1[C:19]([OH:21])=[O:20].[OH-].[K+]>O1CCOCC1.O>[C:1]1([C:17]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][C:18]=2[C:19]([OH:21])=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 109326752-(Cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 574452812-Iodo-5-methanesulfonyl-benzoic acid

Product 1

HCID 59853673HCID 59853673, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

In analogy to a procedure described by Masuda et al. [M. Murata, T. Oyama, S. Watanabe, Y. Masuda, Synthesis 2000, 778] a stirred mixture of 1 eq. 2-cyclohex-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, 0.8 eq. 2-iodo-5-methanesulfonyl-benzoic acid, 2 eq. aqueous 3M KOH solution and 0.03 eq PdCl2 (dppf)2-CHCl3 in dioxane (0.2 ml per mmol) were heated to 80° C. for 5 h. Then the reaction mixture is diluted with water, extracted with AcOEt, the aqueous phase acidified with 2N H2SO4, extracted with AcOEt and the pooled organic extracts dried over Na2SO4, filtered and evaporated. The crude product is purified by flash-chromatography on silica gel with heptane/AcOEt as eluent to yield the title compound; MS (ISN): 279.8 M−H−.

Workup

  1. customIn analogy to a procedure described by Masuda et al. [M. Murata, T. Oyama, S. Watanabe, Y. Masuda, Synthesis 2000, 778]
  2. additiona stirred mixture of 1 eq
  3. extractionextracted with AcOEt
  4. extractionextracted with AcOEt
  5. dry with materialthe pooled organic extracts dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product is purified by flash-chromatography on silica gel with heptane/AcOEt as eluent

Sources & evidence

ORD record
ord-d2ba728d0bd74c78bc181fd8ff39d121
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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