Hydrochloric Acid → HCID 57658756, compound

HRID 910048Notes

Reaction equation

HRID 910048 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[C:14](=[O:21])[C:15]#[C:16][Si](C)(C)C)[CH3:2].CCOCC.Cl>CO>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[C:14](=[O:21])[C:15]#[CH:16])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 57658727HCID 57658727, compound

Product 1

HCID 57658756HCID 57658756, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [4-bromo-2-(3-trimethylsilanylpropynoyl)phenoxy]acetic acid ethyl ester (0.83 g, 2.16 mmol) in methanol (20 mL) was added a 0.1M aqueous solution of Na2B4O7 (10 mL). After stirring for 2-3 minutes at room temperature, Et2O and 1N aq. HCl were added. The phases were separated, and the organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound as yellow oil which crystallized upon standing (0.65 g, 2.09 mmol, 96%). LC/MS (an 10p8) Rt 3.58 min, m/z 311 [M+H]+; 1H NMR (CDCl3): δ1.31 (t, 3H), 3.45 (s, 1H), 4.27 (q, 2H), 4.74 (s, 2H), 6.83 (d, 1H), 7.61 (dd, 1H), 8.14 (d, 1H).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77e1e4ca6c66409f8ae563a181929b1c
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

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