Water → HCID 18600865, compound

HRID 638018Notes

Reaction equation

HRID 638018 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH:14]([OH:35])[C@H:15]1[O:34][C@:16]1([CH3:33])[CH2:17][CH2:18][CH2:19][C@H:20]([CH3:32])[CH2:21][CH2:22][CH2:23][C@H:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>COC(C)(C)C>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[CH:14]([OH:35])[CH2:15][C@:16]([CH3:33])([OH:34])[CH2:17][CH2:18][CH2:19][C@H:20]([CH3:32])[CH2:21][CH2:22][CH2:23][C@H:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 18600864HCID 18600864, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18600865HCID 18600865, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

A solution of 342 mg (0.70 mmol) of (1RS,2R,3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-3,7,11,15-tetramethylhexadecanol in 1 ml of tert.butyl methyl ether was added dropwise at room temperature while stirring to a suspension of 51 mg (2 mmol) of lithium aluminium hydride in 10 ml of tert.butyl methyl ether and the mixture was subsequently stirred at room temperature for a further 1 hour. Then, 0.5 ml of water was added dropwise, the mixture was filtered through sodium sulphate, rinsed with ether and the filtrate was concentrated on a rotary evaporator. The thus-obtained crude produce (341 mg) was chromatographed on silica gel with toluene/ethyl acetate (2:1 parts by volume) and there were obtained 284 mg (84%) of (1RS,3R,7R,11R)-1-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-3,7,11,15-tetramethylhexadecane-1,3-diol, [α]D20 =+0.2° (c=2.16% in chloroform).

Workup

  1. filtrationthe mixture was filtered through sodium sulphate
  2. washrinsed with ether
  3. concentrationthe filtrate was concentrated on a rotary evaporator
  4. customThe thus-obtained crude
  5. customproduce (341 mg)
  6. customwas chromatographed on silica gel with toluene/ethyl acetate (2:1 parts by volume)

Sources & evidence

ORD record
ord-6d5433b228cc4f8891ce1b4c90ad42a8
Source dataset
uspto-grants-1985_12
Patent number
US04559407

Reaction notes

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