Nitrogen → [4-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-methanol

HRID 2065064Notes

Reaction equation

HRID 2065064 reaction equation
N#N.C([Si](C)(C)[O:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]2([CH3:20])[O:19][CH2:18][CH2:17][O:16]2)[CH:14]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(=O)OCC>[CH3:20][C:15]1([C:13]2[CH:14]=[C:10]([CH2:9][OH:8])[S:11][CH:12]=2)[O:16][CH2:17][CH2:18][O:19]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 2724141Tetrabutylammonium FluorideHCID 66928827Tert-butyl-dimethyl-[4-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethoxy]-silane

Product 1

HCID 66929383[4-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of tert-butyl-dimethyl-[4-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethoxy]-silane (545 mg, 1.73 mmol) in dry THF (5.0 mL) was treated at 0° C. with TBAF (2.6 mL of a 1M solution in THF, 2.60 mmol). The reaction mixture was stirred at 0° C. for 2 h. The mixture was then diluted with EA (10 mL), washed with brine (3×20 mL), dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (1:5 EA-Hept) gave the title compound as a colorless oil. TLC: rf (1:1 EA-Hept)=0.36. LC-MS-conditions 02: tR=0.70 min.

Workup

  1. washwashed with brine (3×20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by FC (1:5 EA-Hept)

Sources & evidence

ORD record
ord-5461f226f9744693946205ccbec8ae38
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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