HCID 11016191, compound → (2S)-1,1,2-Triphenyl-1,2-ethanediol

HRID 1700965Notes

Reaction equation

HRID 1700965 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C@H:13]([O:28][C:29](=O)[CH2:30][C@H:31]([OH:40])[C:32]([CH3:39])([CH3:38])/[C:33](/[CH2:36][CH3:37])=[CH:34]/[CH3:35])[C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[OH:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)C>[C:22]1([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:15])[C@H:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[OH:28])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1.[CH3:39][C:32]([CH3:38])(/[C:33](/[CH2:36][CH3:37])=[CH:34]/[CH3:35])[C@@H:31]([OH:40])[CH2:30][CH2:29][OH:28]

Participants

5

Reactant 2

HCID 11016191HCID 11016191, compoundHCID 21226445Aluminium lithium hydride

Product 2

HCID 7000031(2S)-1,1,2-Triphenyl-1,2-ethanediolYield 99%HCID 10954262HCID 10954262, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydnde (1.325 g, 35.0 mmol, 7.0 equiv) is added portionwise to a refluxing solution of (1S)-2,2,1-triphenyl-2-hydroxyethyl (3S,E)-4,4-dimethyl-5-ethyl-3-hydroxy-5-heptenoate 26 (2.364 g, 5.0 mmol) in diethyl ether (50 ml) within a period of 2 h. Refluxing is continued for 30 min. After cooling to 0° C., the reaction is quenched dropwise with 1.35 ml water and 1.35 ml of aqueous NaOH (15%). Diethyl ether (40 ml) and water (2.0 ml) is added. The mixture is stirred for 1 h at r.t. until a white precipitate forms which is filtered off by suction through a small plug of celite. The precipitate is washed with diethyl ether (4×40 ml). The filtrate and the washings are combined and concentrated in vacua. Purification of the residue by flash column chromatography (pentane/diethyl ether 2:1) affords (S)-2,2,1-Triphenyl-ethane-1,2-diol (922 mg, 99%) as a colourless, crystalline solid and (S)-(E)-4,4-Dimethyl-5-ethyl-5-heptene-1,3-diol 28 (836 mg, 90%) as a colourless oil. 13C-NMR (100 MHz, CDCl3): δ=146.2; 121.1; 75.8; 62.6; 44.4; 32.7; 22.8; 21.1; 20.1; 14.3; 13.6

Workup

  1. temperatureRefluxing
  2. customthe reaction is quenched dropwise with 1.35 ml water and 1.35 ml of aqueous NaOH (15%)
  3. additionDiethyl ether (40 ml) and water (2.0 ml) is added
  4. filtrationis filtered off by suction through a small plug of celite
  5. washThe precipitate is washed with diethyl ether (4×40 ml)
  6. concentrationconcentrated in vacua
  7. customPurification of the residue by flash column chromatography (pentane/diethyl ether 2:1)

Sources & evidence

ORD record
ord-0e5c66d636954a108f7b70ee7af9f4c2
Source dataset
uspto-grants-2002_02
Patent number
US06350878B1

Reaction notes

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