Hydrochloric Acid → HCID 20305760, compound

HRID 1732255Notes

Reaction equation

HRID 1732255 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH3:24])[CH2:11][CH2:12][CH2:13][C:14]1([CH3:23])[O:22][CH:15]1[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][Br:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CC[O:28]CC.C(=O)(O)[O-].[Na+]>CC(C)=O.[Cl-].[Na+].O>[CH2:1]([O:8][CH2:9][CH:10]([CH3:24])[CH2:11][CH2:12][CH2:13][C:14]([CH:15]1[O:22][C:18]([CH2:19][Br:20])([OH:21])[CH2:17][CH2:16]1)([OH:28])[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 20305773HCID 20305773, compound

Product 1

HCID 20305760HCID 20305760, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

11-Benzyloxy-1-bromo-6,10-dimethyl-5,6-epoxy-undecan-2-one (16.2 g, 41 mM) in acetone (170.5 ml) is treated with 0.2 N hydrochloric acid (18.75 ml) at 0° C. for 0.75 hours. The reaction mixture is then stirred at room temperature for 18 hours. The solvent is removed in vacuo and the residue obtained is treated with ether, brine and saturated sodium bicarbonate. The phases are separated and the aqueous phase is extracted with ether. The combined extracts are washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give crude 7-benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)-6-methyl-heptan-2-ol (17 g).

Workup

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

Sources & evidence

ORD record
ord-d41d9ee8a1a14d18b38413a8fb8c490c
Source dataset
uspto-grants-1980_12
Patent number
US04237055

Reaction notes

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