Acetic Acid → HCID 66617733, compound

HRID 1295198Notes

Reaction equation

HRID 1295198 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16](=[O:17])[CH:15]2[CH:10]([CH:11]3[CH2:18][CH:14]2[CH:13]=[CH:12]3)[CH:9]1[C:19](C)(C)[O:20][SiH2]C(C)(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:16](=[O:17])[CH:15]2[CH:10]([CH:11]3[CH2:18][CH:14]2[CH:13]=[CH:12]3)[CH:9]1[CH2:19][OH:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 131726522HCID 131726522, compound

Product 1

HCID 66617733HCID 66617733, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 28 (3.2 g; 8.1 mmol) in 60 mL of THF and acetic acid (1.16 mL; 20.3 mmol) was treated with TBAF 1M in THF. The reaction mixture was stirred for 16 h then was diluted with CH2Cl2 (120 mL) and washed with water (75 mL). The organic layer was dried with sodium sulfate and concentrated in vacuo to a yellow oil. Flash chromatography (60% EtOAc/40% hexanes) afforded 1.81 g (81%) of the desired product 29. 1H NMR (CDCl3) δ 6.2 (bs, 1H), 6.1 (bs, 1H), 3.8 (d, 1H), 3.6 (m, 2H), 3.3 (s, 1H), 3.15 (dd, 1H), 3.1 (s, 1H), 2.5 (dd, 1H), 1.5 (app.t, 3H), 1.35 (s, 9H)ppm.

Workup

  1. washwashed with water (75 mL)
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. concentrationconcentrated in vacuo to a yellow oil

Sources & evidence

ORD record
ord-7d74280bf5d445ffa4ae89e2da3ae2e3
Source dataset
uspto-grants-2007_07
Patent number
US07241796B2

Reaction notes

Loading…