Chlorotrimethylsilane → HCID 131735993, compound

HRID 1048732Notes

Reaction equation

HRID 1048732 reaction equation
[CH2:1]([OH:8])[C:2]([NH2:7])([CH2:5][OH:6])[CH2:3][OH:4].[CH3:9][C:10]1([CH3:26])[S:14][C:13]2[C:15]([CH2:24][OH:25])=[C:16]3[S:20][C:19]([CH3:22])([CH3:21])[S:18][C:17]3=[CH:23][C:12]=2[S:11]1.C([Li])CCC.CCCCCC.[CH3:38][Si:39]([CH3:42])([CH3:41])Cl>C(OCC)C>[CH2:1]([OH:8])[C:2]([NH2:7])([CH2:5][OH:6])[CH2:3][OH:4].[CH3:38][Si:39]([CH3:42])([CH3:41])[C:23]1[C:12]2[S:11][C:10]([CH3:26])([CH3:9])[S:14][C:13]=2[C:15]([CH2:24][OH:25])=[C:16]2[C:17]=1[S:18][C:19]([CH3:21])([CH3:22])[S:20]2

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 131735994HCID 131735994, compoundHCID 178418339Butyllithium

Product 1

HCID 131735993HCID 131735993, compoundYield 138.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Compound 1d (0.15 g, 0.17 mmol) was dissolved in dry diethyl ether (5 mL) and tetrametyhlethylendiamine (0.26 mL, 1.69 mmol) was added under argon atmosphere. The mixture was cooled at 0° C., n-butyl lithium 2.5 M in hexane (0.68 mL, 1.69 mmol) was added drop wise over 10 min and the mixture was left to reach RT. After stirring for 3 h at RT, the resulting brown solution was added drop wise at 0° C. to a solution of trimethylchlorosilane (0.65 mL, 5.08 mmol) in diethyl ether (2 mL). The solution was stirred at RT for 4 h and the formation of a white solid was observed. The solid was filtered off, washed with diethyl ether and the organic solution was concentrated under vacuum. The crude product was purified by gravimetric chromatography on silica gel eluting with 15:1 hexanes-ethyl acetate to afford the title compound as an orange powder (0.12 g).

Workup

  1. additiontetrametyhlethylendiamine (0.26 mL, 1.69 mmol) was added under argon atmosphere
  2. waitthe mixture was left
  3. customto reach RT
  4. stirringThe solution was stirred at RT for 4 h
  5. filtrationThe solid was filtered off
  6. washwashed with diethyl ether
  7. concentrationthe organic solution was concentrated under vacuum
  8. customThe crude product was purified by gravimetric chromatography on silica gel eluting with 15:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-debd662043164e99aac25196850e7505
Source dataset
uspto-grants-2016_07
Patent number
US09381257B2

Reaction notes

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