Acetic Anhydride → 3-[1-(Acetamido)tridecyl]-5-trimethylsilylfuran

HRID 1681507Notes

Reaction equation

HRID 1681507 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH:9]([C:22]1[CH:26]=[C:25]([Si:27]([CH3:30])([CH3:29])[CH3:28])[O:24][CH:23]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(N(CC)CC)C>ClCCl>[C:1]([NH:8][CH:9]([C:22]1[CH:26]=[C:25]([Si:27]([CH3:30])([CH3:29])[CH3:28])[O:24][CH:23]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 150370773-(1-Aminotridecyl)-5-trimethylsilylfuran

Product 1

HCID 150370783-[1-(Acetamido)tridecyl]-5-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.1 ml) was added to a solution of 3-(1-aminotridecyl)-5-trimethylsilylfuran (89.8 mg, 0.27 mmol) and triethylamine (0.1 ml) in dichloromethane (1 ml) at room temperature. Stirring was continued overnight (14 hours) while the cooling bath attained room temperature. The residue, after solvent removal, was purified by preparative TLC 20×20 cm, 1000u; developed with 60% ethyl ether/hexane). The title amide was obtained as a pale yellow oil.

Workup

  1. custom(14 hours)
  2. customwhile the cooling bath attained room temperature
  3. customThe residue, after solvent removal
  4. customwas purified by preparative TLC 20×20 cm, 1000u

Sources & evidence

ORD record
ord-173658220ba04466a51d2bcf9a8680d0
Source dataset
uspto-grants-1992_12
Patent number
US05171863

Reaction notes

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