Tetrabutylammonium Fluoride → 2-(3-Hydroxy-2-hydroxymethylpropoxy)-4-methoxy-5-thien-2-ylbenzaldehyde

HRID 347339Notes

Reaction equation

HRID 347339 reaction equation
[Si]([O:8][CH2:9][CH:10]([CH2:28][O:29][Si](C(C)(C)C)(C)C)[CH2:11][O:12][C:13]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[CH:17][C:14]=1[CH:15]=[O:16])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:8][CH2:9][CH:10]([CH2:28][OH:29])[CH2:11][O:12][C:13]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[CH:17][C:14]=1[CH:15]=[O:16]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 161154922-[3-(Tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propoxy]-4-methoxy-5-thien-2-ylbenzaldehyde

Product 1

HCID 161159082-(3-Hydroxy-2-hydroxymethylpropoxy)-4-methoxy-5-thien-2-ylbenzaldehydeYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ex-13E: To a solution of 2-[3-(tert-butyldimethylsilanyloxy)-2-(tert-butyldimethylsilanyloxymethyl)propoxy]-4-methoxy-5-thien-2-ylbenzaldehyde (Ex-13D, 0.78 g, 1.41 mmol) in tetrahydrofuran (5 mL) was added tetrabutylammonium fluoride (1 M in tetrahydrofuran, 3.0 mL, 2.9 mmol) and the mixture was stirred at room temperature for 30 min. The reaction was diluted with ethyl acetate (50 mL) and washed sequentially with a 50% ammonium chloride solution (30 mL), water (2×30 mL), brine (30 mL), dried over sodium sulfate and concentrated to a crude yellow solid. Silica gel chromatography afforded 0.37 g (99%) of 2-(3-hydroxy-2-hydroxymethylpropoxy)-4-methoxy-5-thien-2-ylbenzaldehyde as a pale yellow solid, mp 144–145° C. 1H-NMR (300 MHz, CDCl3) δ 10.33 (s, 1H), 8.10 (s, 1H), 7.38 (dd, 1H, J=3.6, 1.5 Hz), 7.30 (dd, 1H, J=5.1, 1.5 Hz), 7.07 (dd, 1H, J=5.1, 3.6 Hz), 6.59 (s, 1H), 4.35 (d, 2H, J=6.0 Hz), 4.02 (t, 4H, J=4.8 Hz), 3.96 (s, 3H), 2.33 (pentet, 1H, J=6.0 Hz), 1.89 (t, 2H, J=4.8 Hz). Anal. Calcd. for C16H18O5S: C, 59.61; H, 5.63; S, 9.95; Found: C, 59.34; H, 5.75; S, 9.82.

Workup

  1. washwashed sequentially with a 50% ammonium chloride solution (30 mL), water (2×30 mL), brine (30 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to a crude yellow solid

Sources & evidence

ORD record
ord-ab8aca762e0c420cb2a5fccd1d132c4a
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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