Phthalimide → HCID 58027624, compound

HRID 875540Notes

Reaction equation

HRID 875540 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[OH2:12].[C:13]1([CH3:23])[CH:18]=C[C:16](S(O)(=O)=O)=[CH:15][CH:14]=1.[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>O>[OH:12][C@@H:14]([C:15]1[CH:28]=[CH:24][CH:25]=[C:26]([OH:27])[CH:16]=1)[C@H:13]([CH3:23])[CH2:18][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 58027624HCID 58027624, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of THP-protected phenol 81 (4.10 g, 8.51 mmol) and p-toluenesulfonic acid monohydrate (0.36 g, 1.9 mmol) in THF (40 mL) and water (10 mL) was stirred at room temperature for 15 hrs. Solvent was removed in vacuum, the residue was treated with 20% hexane/EtOA. The precipitate was filtered off, washed with hexane, then with 20% EtOAc/hexane. Purification of the precipitate by flash chromatography (40 to 100% EtOAc/hexane gradient) gave the phenol 82 as a white solid. Yield (1.74 g, 83%). 1H NMR (400 MHz, DMSO-d6) δ 9.21 (s, 1H), 7.76-7.83 (m, 4H), 7.05 (t, J=7.8 Hz, 1H), 6.68-6.74 (m, 2H), 6.55 (ddd, J=1.0, 2.4, 8.0 Hz, 1H), 5.26 (d, J=4.1 Hz, 1H), 4.32 (dd, J=4.1, 6.3 Hz, 1H), 3.69 (dd, J=5.1, 13.7 Hz, 1H), 3.42 (dd, J=9.8, 13.5 Hz, 1H), 2.15-2.22 (m, 1H), 0.61 (d, J=6.8 Hz, 3H).

Workup

  1. customSolvent was removed in vacuum
  2. additionthe residue was treated with 20% hexane/EtOA
  3. filtrationThe precipitate was filtered off
  4. washwashed with hexane
  5. customPurification of the precipitate by flash chromatography (40 to 100% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-9b15b6f61ad24e74ae9cc40ca85f9fb4
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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