Tetrabutylammonium Fluoride → HCID 66960230, compound

HRID 1367743Notes

Reaction equation

HRID 1367743 reaction equation
C([Si]([O:8][C:9]1[C:10]([O:32][CH3:33])=[CH:11][C:12]2[CH:13]3[CH:21]([CH2:22][CH2:23][C:24]=2[CH:25]=1)[CH:20]1[C:16]([CH3:31])([CH:17]([O:26][CH2:27][CH2:28][O:29][CH3:30])[CH2:18][CH2:19]1)[CH2:15][CH2:14]3)(C)C)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:33][O:32][C:10]1[C:9]([OH:8])=[CH:25][C:24]2[CH2:23][CH2:22][CH:21]3[CH:13]([CH2:14][CH2:15][C:16]4([CH3:31])[CH:20]3[CH2:19][CH2:18][CH:17]4[O:26][CH2:27][CH2:28][O:29][CH3:30])[C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66958999HCID 66958999, compound

Product 1

HCID 66960230HCID 66960230, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of TBS protected ether 50 (232 mg) in THF (10 mL) was treated with TBAF (0.5 mL, 1M solution in THF). After stirring overnight a standard aqueous work-up was carried out and the desired phenol 51 was purified by column chromatography (4:1 Hex/EA) to give a white solid which showed δH (400 MHz, CDCl3, ref. TMS=0) 6.77 (1H, s, ArH), 6.63 (1H, s, ArH), 5.50 (1H, s, OH), 3.85 (3H, s, ArOMe), 3.41-3.72 (5H, m, 2×OCH2 and CHOR), 3.40 (3H, s, OMe), 2.69-2.83 (6-CH2), 1.16-2.26 (13H, m) and 0.81 (3H, s, 18-Me); δC 144.5, 143.4, 131.7, 129.5 (all C), 114.6, 108.1, 89.6 (all CH), 72.3, 69.5 (both CH2), 59.1 (CH), 56.0 (CH3), 50.3, 44.2 (both CH), 43.3 (C), 38.6 (CH), 38.1, 28.9, 28.1, 27.2, 26.7, 23.0 (all CH2) and 11.6 (CH3).

Workup

  1. customthe desired phenol 51 was purified by column chromatography (4:1 Hex/EA)
  2. customto give a white solid which

Sources & evidence

ORD record
ord-7bdda89f8f77413285dfa9d67b860cb3
Source dataset
uspto-grants-2011_02
Patent number
US07893284B2

Reaction notes

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