Methanol → HCID 70511091, compound

HRID 1732268Notes

Reaction equation

HRID 1732268 reaction equation
C([O:4][CH:5]1[CH2:11][CH2:10]/[C:9](=[CH:12]\[CH2:13][O:14]C(=O)C)/[CH2:8][O:7][C:6]1([CH2:19][CH2:20][CH2:21][CH:22]([CH3:31])[CH2:23][O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[CH3:18])(=O)C.CO.C(=O)([O-])[O-].[K+].[K+]>O>[OH:4][CH:5]1[CH2:11][CH2:10]/[C:9](=[CH:12]\[CH2:13][OH:14])/[CH2:8][O:7][C:6]1([CH2:19][CH2:20][CH2:21][CH:22]([CH3:31])[CH2:23][O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[CH3:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 70511935HCID 70511935, compound

Product 1

HCID 70511091HCID 70511091, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-[(2RS,3SR)-3-acetoxy-6-[(E)-2-acetoxyethylidene]-2-methyl-2-oxepanyl]-2-methyl-1-(tetrahydropyran-2-yloxy)pentane (1.2 g, 2.73 mM), methanol (10 ml) and saturated potassium carbonate (1 ml) and water (1 ml) is stirred under nitrogen at room temperature for three hours. Most of the solvent is removed in vacuo to give a thick oil. This crude material is filtered through a silica gel column (15 g) and washed with ether (100 ml). The solvent is removed in vacuo to give 5-[(2RS,3SR)-3-hydroxy-6-[(E)-2-hydroxyethylidene]-2-methyl-2-oxepanyl]-2-methyl-1-(tetrahydropyran-2-yloxy)pentane (0.953 g, 87%) as a colorless oil.

Workup

  1. customMost of the solvent is removed in vacuo
  2. customto give a thick oil
  3. filtrationThis crude material is filtered through a silica gel column (15 g)
  4. washwashed with ether (100 ml)
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-70e80f3b61bf46e1bfc957671bd1711c
Source dataset
uspto-grants-1980_12
Patent number
US04237054

Reaction notes

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