Tetrabutylammonium Fluoride → 362516-29-8

HRID 1641591Notes

Reaction equation

HRID 1641591 reaction equation
[Si]([O:8][C@H:9]([C@H:17]([O:42][Si](C(C)(C)C)(C)C)[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=[CH:27][C@H:28]([O:34][Si](C(C)(C)C)(C)C)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C@H:9]([C@H:17]([OH:42])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]=[CH:27][C@H:28]([OH:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66735491HCID 66735491, compound

Product 1

HCID 10222011362516-29-8Yield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The product of Step 4 was dissolved in THF (1 mL) and cooled to 0° C. Tetra-butyl ammonium fluoride (10 μL, 0.078 mmol) was added and the reaction mixture was warmed to RT and allowed to stir overnight. The reaction mixture was quenched with saturated ammonium chloride, extracted with ether, dried and concentrated. Purification by preparatory TLC (silica plate, 5% MeOH/Ethyl acetate) afforded 6.1 mg (96.8%) of (5S,6R,E)-methyl 5,6-dihydroxy-8-(2((R,E)-3-hydroxyoct-1-enyl)phenyl)oct-7-enoate. 1H NMR (250 Hz, CDCl3): δ 7.38 (m, 2H), 7.22 (m, 2H), 6.86 (t, J=15.4 Hz, 1H), 6.07 (m, 1H), 4.27 (m, 1H), 3.77 (m, 1H), 3.63 (m, 1H), 3.46 (q, J=14 Hz, 6.9 Hz, 1H), 2.35 (t, J=7.5 Hz, 2H), 1.81-1.53 (m, 4H), 1.32-1.16 (m, 7H), 0.915-0.789 (m, 4H). 13C (500 NMR C6D6): δ 173.79, 136.18, 136.12, 135.98, 131.59, 130.34, 136.18, 131.59, 130.34, 128.53, 128.20, 127.81, 127.68, 127.62, 127.47, 127.13, 76.02, 74.36, 72.65, 51.01, 37.92, 33.83, 32.22, 30.15, 25.58, 23.05, 21.57, 14.24.

Workup

  1. temperaturethe reaction mixture was warmed to RT
  2. customThe reaction mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ether
  4. customdried
  5. concentrationconcentrated
  6. customPurification by preparatory TLC (silica plate, 5% MeOH/Ethyl acetate)

Sources & evidence

ORD record
ord-2f84581c75e84c3d9f3927341333e444
Source dataset
uspto-grants-2012_02
Patent number
US08115023B2

Reaction notes

Loading…