Water → HCID 67824760, compound

HRID 1492116Notes

Reaction equation

HRID 1492116 reaction equation
Br[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:15]1([C:25]([OH:27])=[O:26])[CH2:20][NH:19][CH2:18][CH2:17][N:16]1[C:21]([CH3:24])([CH3:23])[CH3:22])=[N:7]2.[Li]CCCC.[Sn:33](Cl)([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH2:36][CH3:37].O>C1COCC1>[CH2:42]([Sn:33]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:38][CH2:39][CH2:40][CH3:41])[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:15]1([C:25]([OH:27])=[O:26])[CH2:20][NH:19][CH2:18][CH2:17][N:16]1[C:21]([CH3:24])([CH3:23])[CH3:22])=[N:7]2)[CH2:43][CH2:44][CH3:45]

Participants

6

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 53823575HCID 53823575, compoundHCID 178418339Butyllithium

Product 1

HCID 67824760HCID 67824760, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a -100° C. solution of 15 (200 mg, 0.46 mmol) in dry THF (8 ml) was added nBuLi (1.6M, 0.50 mmol, 0.31 ml) dropwise. The resulting black-green solution was stirred for 10 min. at which time Bu3SnCl (0.15 ml, 0.54 mmol) was added neat. The solution was allowed to reach room temperature and stirred 2 h. Water was added and the mixture was extracted with ether. The combined ether extracts were dried (MgSO4) and concentrated to a brown oil. HPLC purification of the oil (Whatman Partisil 10 column, 90:10 CH2Cl2 :EtOAc) afforded the tributylstannyl derivative 16 (150 mg, 50%). 1H NMR d (ppm): 0.85 t (CH3), 1.15-1.55 m (3 CH2), 1.49 s (3 CH3), 3.58 dd (CH2), 3.83 dd (CH2), 7.00 d (CH arom), 7.63 d (CH arom), 8.18 d (CH arom), 8.30 d (CH arom).

Workup

  1. additionwas added neat
  2. customto reach room temperature
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe combined ether extracts were dried (MgSO4)
  5. concentrationconcentrated to a brown oil
  6. customHPLC purification of the oil (Whatman Partisil 10 column, 90:10 CH2Cl2 :EtOAc)

Sources & evidence

ORD record
ord-10ac5e19f6b1451688afc370870741f1
Source dataset
uspto-grants-1994_12
Patent number
US05372813

Reaction notes

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