Ammonium Chloride → HCID 59712306、化合物

HRID 2222436

反応式

HRID 2222436 の反応式
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([O:8][CH3:9])=[O:7].C[Si](C)(C)[N-][SiH3].C[Si](C)(C)[N-][SiH3].[Na+].[Na+].[CH:24]([C:26]1[CH:27]=[CH:28][C:29]([O:41][CH3:42])=[C:30]([CH:40]=1)[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:25].[Cl-].[NH4+]>O1CCCC1>[C:35]([O:34][C:33]([NH:32][CH2:31][C:30]1[CH:40]=[C:26]([CH:24]([OH:25])[C:2]2([C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:4][CH2:5][O:1]2)[CH:27]=[CH:28][C:29]=1[O:41][CH3:42])=[O:39])([CH3:38])([CH3:36])[CH3:37]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 169922Methyl tetrahydrofuran-2-carboxylateHCID 22493931Tert-butyl (5-formyl-2-methoxybenzyl)carbamateHCID 131726863Sodium bis(trimethyldisilylamide)

生成物 1

HCID 59712306HCID 59712306、化合物収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-75 °C

実験手順

A solution of 2.60 g of methyl tetrahydro-2-furancarboxylate in 10 ml of tetrahydrofuran was added dropwise to 20 ml of sodium bis(trimethyldisilylamide) (1 M solution in tetrahydrofuran) cooled to −75° C. under an atmosphere of nitrogen gas, and the reaction mixture was stirred for 30 minutes. A solution of 2.65 g of t-butyl N-(5-formyl-2-methoxybenzyl)carbamate in 20 ml of tetrahydrofuran was added dropwise, and the mixture was stirred further for 1 hour. 200 ml of saturated aqueous ammonium chloride was added, and the mixture was extracted with 200 ml of ethyl acetate. The organic layer washed with 100 ml of brine, dried over magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography, to give 1.934 g of the title compound as a colorless powder.

後処理

  1. stirringthe mixture was stirred further for 1 hour
  2. extractionthe mixture was extracted with 200 ml of ethyl acetate
  3. washThe organic layer washed with 100 ml of brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-e47bf3d96898477598f20f7da2d75b59
出典データセット
uspto-grants-2008_05
特許番号
US07371777B2

関連ノート

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