TBAF tetrahydrofuran → HCID 56607385, compound

HRID 2288096Notes

Reaction equation

HRID 2288096 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:60]([O:61][Si](C(C)(C)C)(C)C)[CH:41]6[CH:42]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[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:69]([CH3:71])[CH3:70])=[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:60]([OH:61])[CH:41]6[CH:42]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[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:69]([CH3:70])[CH3:71])=[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 56613064HCID 56613064, compound

Product 1

HCID 56607385HCID 56607385, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

43.3 mg of compound (51) was stirred together with 435 μl of dry tetrahydrofuran and 65.3 μl of 1M tetrabutylammonium fluoride-tetrahydrofuran solution at room temperature for 1 hour. The reaction solution was concentrated in vacuo to give the crude product. The reaction product was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×20 cm) and eluted with n-hexane-ethyl acetate (8:1) to give 22.5 mg of compound (52) as a colorless oily substance.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customto give the crude product
  3. additionThe reaction product was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×20 cm)
  4. washeluted with n-hexane-ethyl acetate (8:1)

Sources & evidence

ORD record
ord-17fa375c768a4ab8ae312ed90a538ab9
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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