Sodium Iodide → HCID 19836671, compound

HRID 476885Notes

Reaction equation

HRID 476885 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:22][CH:21]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 198366434-({[tert-Butyl(diphenyl)silyl]oxy}methyl)phenol

Product 1

HCID 19836671HCID 19836671, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Step A ##STR104## A solution of 4-tert-butyldiphenylsilyloxymethylphenol (see Example 1, Step A) (13 g) and ethyl bromoacetate (4.0 ml) in acetone (50 ml) was refluxed for 40 h in the presence of sodium iodide (5.37 g) and potassium carbonate (4.69 g). The reaction mixture was partitioned between ethyl ether and water, and the dried (MgSO4) organic phase was evaporated. Silica gel chromatography of the residue afforded ethyl 2-(4-tert-butyldiphenylsilyloxymethylphenyl)oxyacetate as a colourless syrup (8 g); IR νmax 1735 cm-1 ; NMR (60 MHz, CDCl3)δ 1.1 (9H, s), 1.3 (3H, t, J=6 Hz), 4.2 (2H, q, J=6 Hz), 4.55 and 4.65 (each 2H, s), 6.8-7.8 (10H, m).

Workup

  1. customThe reaction mixture was partitioned between ethyl ether and water
  2. dry with materialthe dried (MgSO4) organic phase
  3. customwas evaporated

Sources & evidence

ORD record
ord-b0b2e54ff82c40229a733b8d1d2af9e7
Source dataset
uspto-grants-1989_12
Patent number
US04886793

Reaction notes

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