Dibutyltin dichloride → HCID 66648191, compound

HRID 417939Notes

Reaction equation

HRID 417939 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[C:19](=[O:20])[CH2:18][C:17]([CH3:22])([CH3:21])[CH2:16][C:14]=4[N:15]=3)[C:6]=2[CH:23]=1.[O:24]1[CH2:28][CH2:27][CH:26]([CH:29]=O)[CH2:25]1.C1([SiH3])C=CC=CC=1.C([Sn](Cl)(Cl)CCCC)CCC>C1COCC1>[CH3:22][C:17]1([CH3:21])[CH2:16][C:14]2[N:15]=[C:11]([N:7]3[C:6]4[CH:23]=[C:2]([NH:1][CH2:29][CH:26]5[CH2:27][CH2:28][O:24][CH2:25]5)[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)[S:12][C:13]=2[C:19](=[O:20])[CH2:18]1

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 24956161HCID 24956161, compound

Product 1

HCID 66648191HCID 66648191, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 12 (50 mg, 0.15 mmol), tetrahydrofuran-3-carboxaldehyde (30 mg, 0.15 mmol), phenylsilane (0.04 mL, 0.3 mmol) and dibutyltin dichloride (5 mg, 0.015 mmol) in THF (3 mL) was heated to 100° C. under microwave irradiation for 40 min. After cooling to r.t., the mixture was partitioned between EtOAc (50 mL) and water (50 mL). The organics were washed with brine (50 mL), dried (MgSO4) and concentrated in vacuo. The crude material was purified by prep HPLC to give the title compound as a yellow solid (14 mg, 22%). δH (CDCl3) 1.08 (6H, s), 1.56-1.71 (2H, m), 1.98-2.13 (1H; m), 2.35 (2H, s), 2.43-2.57 (1H, m), 2.68 (2H, s), 3.03 (1H, d, J 6.8 Hz), 3.52-3.59 (1H, m), 3.65-3.76 (1H, m), 3.78-3.91 (2H, m), 4.08-4.15 (2H, m), 4.16-4.22 (2H, m), 6.32 (1H, dd, J 8.7, 2.4 Hz), 6.73 (1H, d, J 8.7 Hz), 7.10 (1H, d, J 2.6 Hz). LCMS (ES+) 414 (M+H)+.

Workup

  1. customthe mixture was partitioned between EtOAc (50 mL) and water (50 mL)
  2. washThe organics were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by prep HPLC

Sources & evidence

ORD record
ord-3339ba47d4d34ab5a937fa69840652e0
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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