tert-Butyl((4,4-difluoro-4,5-dihydrofuran-2-yl)methoxy)dimethylsilane → Furan, 2-[[[(1,1-diMethylethyl)diMethylsilyl]oxy]Methyl]-4-fluoro-

HRID 1363293Notes

Reaction equation

HRID 1363293 reaction equation
[C:1]([Si:5]([O:8][CH2:9][C:10]1[O:11][CH2:12][C:13](F)([F:15])[CH:14]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[C:1]([Si:5]([O:8][CH2:9][C:10]1[O:11][CH:12]=[C:13]([F:15])[CH:14]=1)([CH3:7])[CH3:6])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 59648514tert-Butyl((4,4-difluoro-4,5-dihydrofuran-2-yl)methoxy)dimethylsilane

Product 1

HCID 59648516Furan, 2-[[[(1,1-diMethylethyl)diMethylsilyl]oxy]Methyl]-4-fluoro-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl((4,4-difluoro-4,5-dihydrofuran-2-yl)methoxy)dimethylsilane was diluted with DCM and treated with silica gel (5 g SiO2/1 g of compound). The flask was swirled around to ensure an even mix, DCM was allowed to air dry and the flask left at rt overnight. The silica gel was transferred to a fritted funnel and eluted with DCM until no more product could be detected by TLC. The filtrate was concentrated to provide an orange oil tert-butyl((4-fluorofuran-2-yl)methoxy)dimethylsilane. 1H NMR (400 MHz, CDCl3) δ 0.09 (s, 6H), 0.91 (s, 9H), 4.55 (br s, 2H), 6.20 (m, 1H), 7.31 (dd, J=5.03, 0.63 Hz, 1H); 19F NMR (376.19 MHz, CDCl3) δ −170.53 (dd, J=4.95, 1.32, 1F).

Workup

  1. additiontreated with silica gel (5 g SiO2/1 g of compound)
  2. additionan even mix
  3. customto air dry
  4. customThe silica gel was transferred to a fritted funnel
  5. washeluted with DCM until no more product
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-eecdc5764c114d84ae77ffe0b38578f8
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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