TBAF tetrahydrofuran → HCID 56637837, compound

HRID 2288081Notes

Reaction equation

HRID 2288081 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]23[C:28]4([CH:30]=[O:31])[CH2:29][CH:20]([C:21]2([CH2:33][O:34][C:35]25[CH:47]([O:48][Si](C(C)(C)C)(C)C)[CH:41]6[CH:42]([O:43][CH:44]([CH3:46])[CH3:45])[CH:37]([CH:38]([O:40]6)[O:39]2)[O:36]5)[CH2:22][CH:23]2[CH:27]4[CH2:26][CH2:25][CH:24]2[CH3:32])[CH:19]=[C:18]3[CH:56]([CH3:58])[CH3:57])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>O1CCCC1>[C:1]1([CH:7]([O:14][C:15]([C:17]23[C:28]4([CH:30]=[O:31])[CH2:29][CH:20]([C:21]2([CH2:33][O:34][C:35]25[CH:47]([OH:48])[CH:41]6[CH:42]([O:43][CH:44]([CH3:45])[CH3:46])[CH:37]([CH:38]([O:40]6)[O:39]2)[O:36]5)[CH2:22][CH:23]2[CH:27]4[CH2:26][CH2:25][CH:24]2[CH3:32])[CH:19]=[C:18]3[CH:56]([CH3:58])[CH3:57])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 56634327HCID 56634327, compound

Product 1

HCID 56637837HCID 56637837, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13 mg of compound (33) was mixed with 200 μl of tetrahydrofuran and 14.8 μl of 1M tetrabutylammonium fluoride-tetrahydrofuran solution, and the reaction was conducted at room temperature under stirring for 15 hours. The reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm) and eluted with n-hexane-ethyl acetate (2:1). The fraction containing the desired product was concentrated to dryness to give 9.0 mg of compound (34).

Workup

  1. customwas conducted at room temperature
  2. additionThe reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm)
  3. washeluted with n-hexane-ethyl acetate (2:1)
  4. additionThe fraction containing the desired product
  5. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-89f1736cad8144088ca459b784a0fb4a
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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