Hydrochloric Acid → Adamantane-1,4-diol

HRID 1752308

反応式

HRID 1752308 の反応式
[BH4-].[Na+].[OH:3][C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([C:7]3=[O:14])[CH2:5]1)[CH2:11]2.Cl>CO>[C:4]12([OH:3])[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH:7]3[OH:14])[CH2:5]1)[CH2:11]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 64184IdramantoneHCID 4311764Sodium borohydride

生成物 1

HCID 4252005Adamantane-1,4-diol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium borohydride (3.00 g) is added in three equal portions to a solution of 5-hydroxy-adamantan-2-one (5.00 g) in methanol (100 mL) chilled in an ice bath. The mixture is stirred in the cooling bath for 1 h and at room temperature overnight. 1 M hydrochloric acid is added and the resulting mixture is stirred for 0.5 h. The mixture is concentrated, water is then added to the residue, and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (MgSO4), and concentrated to give the title compound as a mixture of diastereomers (ca. 1:1). Yield: 3.20 g (63% of theory); Mass spectrum (ESI+): m/z=186 [M+NH4]+.

後処理

  1. temperaturechilled in an ice bath
  2. stirringthe resulting mixture is stirred for 0.5 h
  3. concentrationThe mixture is concentrated
  4. additionwater is then added to the residue
  5. extractionthe resulting mixture is extracted with ethyl acetate
  6. extractionThe combined extract
  7. washis washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-1213e1f4b2cc4e078632bce8edeca8f8
出典データセット
uspto-grants-2015_10
特許番号
US09163012B2

関連ノート

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