TBAF tetrahydrofuran → HCID 15459998, compound

HRID 2288092Notes

Reaction equation

HRID 2288092 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:50]([O:51][Si](C(C)(C)C)(C)C)[CH:41]6[CH:42]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[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:59]([CH3:61])[CH3:60])=[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:50]([OH:51])[CH:41]6[CH:42]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[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:59]([CH3:60])[CH3:61])=[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 56621033HCID 56621033, compound

Product 1

HCID 15459998HCID 15459998, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

18.7 mg of compound (45) was stirred together with 218 μl of dry tetrahydrofuran and 32.7 μl of 1M tetrabutylammonium fluoride-tetrahydrofuran solution at room temperature for 4 hours. The reaction solution was concentrated in vacuo to give the crude reaction product. It 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 16.3 mg of compound (46) as a colorless oily substance.

Workup

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

Sources & evidence

ORD record
ord-f03f582e8ee04bee91d3306777266a16
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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