Hydrochloric Acid → 1,4-Dioxaspiro(4.5)decan-8-ol

HRID 399106

反応式

HRID 399106 の反応式
[B-].[Na+].[CH2:3]1[O:13][C:6]2([CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]2)[O:5][CH2:4]1.Cl>CO>[CH2:4]1[O:5][C:6]2([CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2)[O:13][CH2:3]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 22959485Vertellus

生成物 1

HCID 5673521,4-Dioxaspiro(4.5)decan-8-ol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium borohydrate (2.4 g, 64 mmol) was added in portions to a stirred ice cold solution of 1,4 cyclohexanedione monoethylene ketal 38 (20 g, 128 mmol) in 60 mL of methanol (Step 35). After addition was complete, 1N HCl was added to the solution dropwise until a pH of 8 was obtained and then the solvent was removed by roto-evaporation. The product 39 (16.8 g, 84%) showed a single spot on TLC (Rf=0.4, ethyl acetate/hexane 20:80 solvent system, visualization was with acidic vanillin ethanol solution) and was used without further purification. 1H NMR (CDCl3) δ1.6-1.9 (m, 8H, ring-CH2), 3.8 (m, 1H, CH--O), 4.0 (s, 4H, ketal-CH2), 5.3 (s, 1H, OH).

後処理

  1. additionAfter addition
  2. customwas obtained
  3. customthe solvent was removed by roto-evaporation
  4. customwas used without further purification

出典と根拠

ORDレコード
ord-f7bb252431bb48619f23732c50a5aaa1
出典データセット
uspto-grants-1998_10
特許番号
US05817776

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