Trimethyl orthoformate → HCID 20305770, compound

HRID 1732256Notes

Reaction equation

HRID 1732256 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH3:25])[CH2:11][CH2:12][CH2:13][C:14]([CH:17]1[O:21][C:20]([CH2:23][Br:24])([OH:22])[CH2:19][CH2:18]1)([OH:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26]OC(OC)OC.S(=O)(=O)(O)O.CO.C(=O)(O)[O-].[Na+]>[Cl-].[Na+].O.CCOCC>[CH2:1]([O:8][CH2:9][CH:10]([CH3:25])[CH2:11][CH2:12][CH2:13][C:14]([CH:17]1[O:21][C:20]([CH2:23][Br:24])([O:22][CH3:26])[CH2:19][CH2:18]1)([OH:16])[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 18363649Sulfuric acid methanolHCID 20305760HCID 20305760, compound

Product 1

HCID 20305770HCID 20305770, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

7-Benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)-6-methyl-heptan-2-ol (16.9 g, 41 mM) is treated with distilled trimethylorthoformate (51 ml, 66 mM) and 0.1 N sulfuric acid/methanol (15.3 ml) at 0° C. for 0.5 hours and then at 5° C. for 66 hours. The solvent is removed in vacuo and the residue obtained is treated with ether, saturated sodium bicarbonate and brine. The layers are separated, the aqueous phase is extracted with ether and the combined ether extracts are washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give crude 7-benzyloxy-2-[2-bromomethyl-2-methoxy-tetrahydrofuran-5-yl]-6-methyl-heptan-2-ol.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue obtained
  3. customThe layers are separated
  4. extractionthe aqueous phase is extracted with ether
  5. washthe combined ether extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-91cd4a7011334c218d77f693b3f200c7
Source dataset
uspto-grants-1980_12
Patent number
US04237055

Reaction notes

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