Hydrochloric Acid → 11-hydroxy-3Z-dodecenoic acid

HRID 638140

反応式

HRID 638140 の反応式
[H][H].[BH4-].[Na+].C(N)CN.[OH:9][CH:10]([CH3:23])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[C:18][CH2:19][C:20]([OH:22])=[O:21].Cl>C(O)C.[OH-].[Na+].[Cl-].[Na+].O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[OH:9][CH:10]([CH3:23])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[C:20]([OH:22])=[O:21]

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 108999303-Dodecynoic acid, 11-hydroxy-HCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 8674056011-hydroxy-3Z-dodecenoic acid収率 96.4%

試薬・触媒・溶媒 4

HCID 9756Nickel Acetate触媒HCID 702Ethanol溶媒2 回HCID 14798Sodium Hydroxide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
23 °C

実験手順

To a vigorously stirred mixture of nickel acetate (1 g) and absolute ethanol (25 mL), saturated with hydrogen, was added 5 mL of the filtrate from a solution of sodium borohydride (500 mg) in ethanol (12 mL) and 2N aqueous sodium hydroxide (0.63 mL). After hydrogen evolution had ceased, the black suspension was treated with 0.7 mL of ethylene diamine.6Alkyne 24 (643 mg, 3.0 mmol) was added and the reaction stirred for 1 hr at 23° C. The reaction was diluted with brine (100 mL), acidified with 5% HCl and extracted with ether (4×50 mL). The ether extract was washed with brine (2×50 mL). Product isolation gave 620 mg of 26 (96% yield).

後処理

  1. extractionextracted with ether (4×50 mL)
  2. extractionThe ether extract
  3. washwas washed with brine (2×50 mL)

出典と根拠

ORDレコード
ord-6d96527de97c44c283ca96f9c8228bd4
出典データセット
uspto-grants-1985_12
特許番号
US04560551

関連ノート

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