HCID 59523110, compound → HCID 59523108, compound

HRID 1424774Notes

Reaction equation

HRID 1424774 reaction equation
[CH2:1]([O:13][C:14]1[N:15]=[C:16]([Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[S:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Li][CH2:30][CH2:31][CH2:32][CH3:33]>C1COCC1>[CH2:1]([O:13][C:14]1[N:15]=[C:16]([Si:19]([CH:26]([CH3:27])[CH3:28])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:21])[CH3:22])[S:17][C:18]=1[C:18]1[S:17][C:16]([Si:19]([CH:23]([CH3:24])[CH3:25])([CH:26]([CH3:27])[CH3:28])[CH:20]([CH3:22])[CH3:21])=[N:15][C:14]=1[O:13][CH2:30][CH2:31][CH2:32][CH2:33][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 59523110HCID 59523110, compoundHCID 178418339Butyllithium

Product 1

HCID 59523108HCID 59523108, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6.24 g (14.7 mmol) of compound 11 in 150 mL of THF was cooled to −78° C. and treated dropwise with 6.45 mL (16.1 mmol) of n-BuLi (2.5 M in hexanes). The mixture was stirred for 45 minutes, then the dry ice bath was removed and the mixture was stirred at ambient temperature for 1 hour. The mixture was cooled to 0° C. and treated with 5.69 g (16.1 mmol) of Fe(acac)3 (Strem Chemicals, Inc.). The mixture was heated in an 80° C. oil bath for 2 h, cooled to room temperature, and filtered. The filter cake was washed with 3×25 mL of THF. The filtrate was concentrated in vacuo and purified by flash chromatography (silica gel, 5.5×35 cm, chloroform) to give 6.0 g (96% yield) of compound 12 as a yellow oil. 1H NMR (500 MHz) δ 4.51 (t, 4H, J=6.3 Hz), 1.86-0.88 (m, 88H).

Workup

  1. customthe dry ice bath was removed
  2. stirringthe mixture was stirred at ambient temperature for 1 hour
  3. temperatureThe mixture was heated in an 80° C. oil bath for 2 h
  4. temperaturecooled to room temperature
  5. filtrationfiltered
  6. washThe filter cake was washed with 3×25 mL of THF
  7. concentrationThe filtrate was concentrated in vacuo
  8. custompurified by flash chromatography (silica gel, 5.5×35 cm, chloroform)

Sources & evidence

ORD record
ord-8b7729feeeb04d1d8f52fd91f45ad6cd
Source dataset
uspto-grants-2015_01
Patent number
US08927971B2

Reaction notes

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