Sodium Iodide → HCID 19836671、化合物

HRID 476885ノート

反応式

HRID 476885 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 19836671HCID 19836671、化合物

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-b0b2e54ff82c40229a733b8d1d2af9e7
出典データセット
uspto-grants-1989_12
特許番号
US04886793

反応ノート

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