Dibutyltin oxide → HCID 178471346, compound

HRID 1927438Notes

Reaction equation

HRID 1927438 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5][CH:4]=1)#[N:2].C[Si]([N:45]=[N+:46]=[N-:47])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[C:35]1([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2/[CH:22]=[CH:21]/[CH:11]([CH2:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]3[NH:47][N:46]=[N:45][N:2]=3)=[CH:4][CH:5]=2)[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57831356Ethyl (7E)-6-[2-(4-cyanophenyl)ethyl]-8-{2-[(5-phenylpentyl)oxy]phenyl}oct-7-enoate

Product 1

HCID 178471346HCID 178471346, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 128 mg (0.24 mmol) of ethyl (7E)-6-[2-(4-cyanophenyl)ethyl]-8-{2-[(5-phenylpentyl)oxy]phenyl}oct-7-enoate in 10 ml of toluene is mixed with 0.47 ml (3.57 mmol) of trimethylsilyl azide and 88.9 mg (0.36 mmol) of di-n-butyltin oxide and heated at 80° C. for 12 hours. After cooling to room temperature, the mixture is washed with saturated sodium bicarbonate solution. The organic phase is separated off, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the filtrate is concentrated to dryness. The resulting crude product is purified by preparative HPLC. 62 mg (0.11 mmol, 44.8% of theory) of a colorless foam are obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe mixture is washed with saturated sodium bicarbonate solution
  3. customThe organic phase is separated off
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated to dryness
  8. customThe resulting crude product is purified by preparative HPLC
  9. custom62 mg (0.11 mmol, 44.8% of theory) of a colorless foam are obtained

Sources & evidence

ORD record
ord-b1cbc7710c284cb49523201e54df4878
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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