Tributylstannane → HCID 68865301, compound

HRID 1725998Notes

Reaction equation

HRID 1725998 reaction equation
[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].[CH2:15]([SnH:19]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>CC(N=NC(C#N)(C)C)(C#N)C>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])/[CH:5]=[CH:4]/[CH2:3][CH2:2][C:1]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:6])[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 561097Benzyl 4-pentynoate

Product 1

HCID 68865301HCID 68865301, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6547AzobisisobutyronitrileCatalyst

Procedure

A mixture of Example 510B (8.7017 g, 46.23 mmol), tributyltin hydride (14.5 mL, 54.09 mmol), and AIBN (228 mg, 1.39 mmol) was stirred at 80° C. for 24 hours, cooled to room temperature, and purified by flash column chromatography to provide the desired product (16.4529 g, 74%). 1H NMR (300 MHz, DMSO-d6) δ 7.35 (m, 5H), 5.93 (m, 1H), 5.09 (m, 1H), 5.07 (s, 2H), 2.44 (m, 2H), 2.38 (m, 2H), 1.45 (m, 6H), 1.25 (m, 6H), 0.85 (m, 15H).

Workup

  1. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-cd475e60ccbe47d1acc972c042dc25a4
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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