Tributylstannane → HCID 16664549, compound

HRID 1869126Notes

Reaction equation

HRID 1869126 reaction equation
[CH2:1]([O:8][N:9]([CH2:22][C:23]#[C:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([SnH:37]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH3:36]>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:8][N:9]([CH2:22]/[CH:23]=[C:24](\[P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])/[Sn:37]([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:33][CH2:34][CH2:35][CH3:36])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 16664548HCID 16664548, compound

Product 1

HCID 16664549HCID 16664549, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Diethyl 3-[N-benzyloxy,N-(2-nitrobenzenesulfonyl)amino]-propynylphosphonate (109) (10.4 g, 21.6 mmol) and Tetrakis(triphenylphosphine)-palladium(0) (Pd(PPh3)4) (474 mg, 0.430 mmol) in dry THF (100 mL) was added tributyltin hydride (BU3SnH) (6.28 g, 21.6 mmol) over a period of 40 min at 0° C. The reaction mixture was stirred at 0° C. for one hour and was allowed to warm to room temperature over a period of time of 2 hours. The solvent was removed under reduced pressure and the crude oil was purified by column chromatography using a mixture of pentane/acetone (volume ratio 3/1), yielding 15 g of an amber oil (90%).

Workup

  1. temperatureto warm to room temperature over a period of time of 2 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe crude oil was purified by column chromatography
  4. additiona mixture of pentane/acetone (volume ratio 3/1)

Sources & evidence

ORD record
ord-0c1376e2e01c4e1881f9ed9dfd015f16
Source dataset
uspto-grants-2009_12
Patent number
US07638505B2

Reaction notes

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