Sodium Hydroxide → 6-(5-Carboxy-5-phenyl-hexylsulfanyl)-2-methyl-2-phenyl-hexanoic acid

HRID 48316ノート

反応式

HRID 48316 の反応式
C([O:3][C:4](=[O:35])[C:5]([CH3:34])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:23]([O:25]CC)=[O:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])C.[OH-].[Na+]>C(O)C.O>[C:4]([C:5]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:34])[CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:16])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]([OH:25])=[O:24])([OH:35])=[O:3]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 116418176-(5-Ethoxycarbonyl-5-phenylhexylsulfanyl)-2-methyl-2-phenylhexanoic acid ethyl ester

生成物 1

HCID 102971706-(5-Carboxy-5-phenyl-hexylsulfanyl)-2-methyl-2-phenyl-hexanoic acid収率 68.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A solution of 6-(5-ethoxycarbonyl-5-phenylhexylsulfanyl)-2-methyl-2-phenylhexanoic acid ethyl ester (6.00 g, 12.0 mmol) and sodium hydroxide (3.1 g, 74.0 mmol) in ethanol (40 mL) and deionized water (4 mL) was heated to reflux for 2 h. The ethanol was evaporated in vacuo and the residue was dissolved in water (20 mL) and extracted with diethyl ether (20 mL). The organic phase was discarded. The aqueous layer was acidified with 2 N hydrochloric acid (15 ml) to pH 2-3 and extracted with diethyl ether (4′ 50 mL). The combined organic layers were washed with brine (15 mL), dried over MgSO4, and concentrated in vacuo. The residue (4.53 g) was purified by column chromatography on silica gel (hexanes/ethyl acetate=10/1) to give 6-(5-carboxy-5-phenyl-hexylsulfanyl)-2-methyl-2-phenyl-hexanoic acid (3.63 g, 68%) as a yellowish oil. 1H NMR (300 MHz, CDCl3/TMS): d (ppm): 7.42-7.20 (m, 10H), 2.45 (t, J=7.3 Hz, 4H), 2.15-1.80 (m, 4H), 1.65-1.45 (m, 4H), 1.56 (s, 6H), 1.40-1.15 (m, 4H). 13C NMR (75 MHz, CDCl3/TMS): d (ppm): 182.43, 142.89, 128.41, 126.91, 126.05, 50.00, 38.53, 31.80, 30.00, 24.03, 22.40. HRMS (LSIMS, nba): Calcd. for C26H35O4S1 (MH+): 443.2256, found: 443.2231.

後処理

  1. temperatureto reflux for 2 h
  2. customThe ethanol was evaporated in vacuo
  3. dissolutionthe residue was dissolved in water (20 mL)
  4. extractionextracted with diethyl ether (20 mL)
  5. extractionextracted with diethyl ether (4′ 50 mL)
  6. washThe combined organic layers were washed with brine (15 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue (4.53 g) was purified by column chromatography on silica gel (hexanes/ethyl acetate=10/1)

出典と根拠

ORDレコード
ord-78e05ab6bfa14117b27204f62c1b9645
出典データセット
uspto-grants-2004_03
特許番号
US06703422B2

反応ノート

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