Ammonium Chloride → HCID 131719623、化合物

HRID 481991ノート

反応式

HRID 481991 の反応式
Cl[C@H:2]([Br:21])[CH2:3][CH2:4][CH2:5][CH2:6][B:7]([O:9][C:10]12[CH2:18][CH:14]([C:15]1([CH3:17])[CH3:16])[CH2:13][CH2:12][C:11]2([OH:20])[CH3:19])[OH:8].[CH3:22][Mg].[Cl-].[NH4+]>C1COCC1>[C:10]12([OH:9])[CH2:18][CH:14]([C:15]1([CH3:17])[CH3:16])[CH2:13][CH2:12][C:11]2([OH:20])[CH3:19].[Br:21][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([B:7]([O-:8])[O-:9])[CH3:22]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 131719624HCID 131719624、化合物HCID 178477778HCID 178477778、化合物

生成物 1

HCID 131719623HCID 131719623、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

In a 500 ml round bottomed flask, 300 ml of anhydrous THF and the crude pinanediol (R)-1-chloro-5-bromopentylboronate from the previous reaction (assuming 89 g; 0.247 moles) were mixed and cooled to -78° C. with stirring under argon. To the solution was added methylmagnesium bromnide (3.26N, 79.6 ml). The solution was warmed to room temperature overnight. Petroleum ether (500 ml) and saturated ammonium chloride (250 ml) were added, forming an emulsion. The aqueous phases were separated. The organic phase was washed with saturated ammonium chloride (2×250 ml), causing the emulsion to disappear. The combined aqueous phases were washed with petroleum ether (2×250 ml). The combined organic phases were dried over sodium sulfate, filtered and evaporated under vacuum to yield 85.85 g of crude pinanediol (R)-5-bromo-1-methylpentylboronate.

後処理

  1. additionwere mixed
  2. temperatureThe solution was warmed to room temperature overnight
  3. customforming an emulsion
  4. customThe aqueous phases were separated
  5. washThe organic phase was washed with saturated ammonium chloride (2×250 ml)
  6. washThe combined aqueous phases were washed with petroleum ether (2×250 ml)
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under vacuum

出典と根拠

ORDレコード
ord-2d0550abe54343ca8e315b63e24a2ec3
出典データセット
uspto-grants-1998_08
特許番号
US05792772

反応ノート

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