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

HRID 638140

반응식

HRID 638140 반응식
[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]

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 108999303-Dodecynoic acid, 11-hydroxy-HCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 8674056011-hydroxy-3Z-dodecenoic acid수율 96.4%

시약·촉매·용매 4

HCID 9756Nickel Acetate촉매HCID 702Ethanol용매2회HCID 14798Sodium Hydroxide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
23 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-6d96527de97c44c283ca96f9c8228bd4
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04560551

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