Water → HCID 68379485, compound

HRID 1410059Notes

Reaction equation

HRID 1410059 reaction equation
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][CH:7]=1)=[O:5].[Li+].CC([N-]C(C)C)C.[CH3:40][C:41]1([CH3:56])[C:45]([CH3:47])([CH3:46])[O:44][B:43]([C:48]2[CH:49]=[C:50]([CH:53]=[CH:54][CH:55]=2)[CH:51]=O)[O:42]1.O>C1COCC1>[CH3:46][C:45]1([CH3:47])[C:41]([CH3:40])([CH3:56])[O:42][B:43]([C:48]2[CH:49]=[C:50]([CH:53]=[CH:54][CH:55]=2)/[CH:51]=[CH:10]/[C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH3:2])=[O:5])=[CH:31][CH:30]=2)[O:44]1

Participants

6

Reactant 4

HCID 962WaterHCID 2724682Lithium diisopropylamideHCID 27605863-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehydeHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

Product 1

HCID 68379485HCID 68379485, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of (4-(methoxycarbonyl)benzyl)triphenylphosphonium bromide (2.9 g, 6 mmol) in 50 mL of THF was added dropwise via syringe to a solution of LDA (5 mL, 10 mmol) in THF at −78° C. under N2 atmosphere. After 30 min at this temperature 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (1.4 g, 6 mmol) in 50 mL of THF was added dropwise via syringe and then stirred at this temperature for 30 min and then allow warm to room temperature over 4 hours, and stirred overnight. The mixture was poured into H2O (300 mL) and then extracted with ethyl acetate (3×100 mL). The combined organic layer was concentrated and purified by silica gel chromatography (eluting with a mixture of petroleum ether and ethyl acetate=50:1) to give (E)-methyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl)benzoate (0.9 g, 41%) as a colorless oil. LC-MS: 365 [M+H]+, tR=1.98 min.

Workup

  1. stirringstirred overnight
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. concentrationThe combined organic layer was concentrated
  4. custompurified by silica gel chromatography (
  5. washeluting with a mixture of petroleum ether and ethyl acetate=50:1)

Sources & evidence

ORD record
ord-8a9e8380ce3c4b638057afa4c7f72d9e
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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