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tert-Butyl methyl ether → Tert-butyl 2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]-2-methylpropionate

HRID 854645
ノート
印刷プレビュー

反応式

HRID 854645 の反応式
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([CH2:8][O:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.[H-].[Na+].[CH3:22][C:23]1[O:27][C:26]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)=[N:25][C:24]=1[CH2:35]I.C(OC)(C)(C)C>CN(C)C=O.O>[CH3:22][C:23]1[O:27][C:26]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)=[N:25][C:24]=1[CH2:35][O:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([CH2:8][O:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 219803112-(4-Methylphenyl)-4-iodomethyl-5-methyloxazoleHCID 67214679Tert-butyl 2-(cis-3-hydroxycyclohexylmethoxy)-2-methylpropionate

生成物 1

HCID 69242284Tert-butyl 2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]-2-methylpropionate収率 71.4%

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

50 mg of tert-butyl 2-(cis-3-hydroxycyclohexylmethoxy)-2-methylpropionate are dissolved in 0.5 ml of dimethylformamide and 22 mg of NaH (60%) are added. After 30 min of stirring, 112 mg of 5-methyl-2-p-tolyloxazol-4-yl-methyl iodide are added at room temperature. The mixture is placed in an ultrasonic bath for 10 min and then stirred at room temperature for 3 h. 10 ml of methyl tert-butyl ether and 10 ml of water are then added. The phases are separated, the aqueous phase is extracted once with methyl tert-butyl ether and the organic phases are dried over MgSO4 and concentrated. The residue is chromatographed on silica gel (heptane/ethyl acetate 5/1->1/1). 60 mg of the crude tert-butyl 2-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethoxy]-2-methylpropionate are obtained as a yellow oil. C27H39NO5 (457), LCMS(ESI): 458 (MH+).

後処理

  1. waitThe mixture is placed in an ultrasonic bath for 10 min
  2. stirringstirred at room temperature for 3 h
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted once with methyl tert-butyl ether
  5. dry with materialthe organic phases are dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (heptane/ethyl acetate 5/1->1/1)

出典と根拠

ORDレコード
ord-835575b6232145238a0e1bfe12e609e9
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07259177B2

反応ノート

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