Ethanol → HCID 59354861, compound

HRID 1776296Notes

Reaction equation

HRID 1776296 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:22])[C:16]#[C:17][C:18](O)([CH3:20])[CH3:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(CC)CC.CC[OH:30]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:22][C:18]([CH3:19])([CH3:20])[C:17](=[O:30])[CH:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8021DiethylamineHCID 59354820HCID 59354820, compound

Product 1

HCID 59354861HCID 59354861, compoundYield 98%

Procedure

To a RT solution of 1-(4-(benzyloxy)phenyl)-4-hydroxy-4-methylpent-2-yn-1-one (1.5 g, 0.005 mol) in EtOH (10 mL) was added a solution of Et2NH (0.86 mL) in EtOH (10 mL) under an inert atmosphere. The reaction mixture was stirred for 1 hr and then concentrated in vacuo to obtain the crude product. The crude material was partitioned between water and DCM and the organic layer was separated, washed with water, dried over Na2SO4 and then concentrated in vacuo to afford 5-(4-(benzyloxy)phenyl)-2,2-dimethylfuran-3(2H)-one (1.4 g, 98%) as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain the crude product
  3. customThe crude material was partitioned between water and DCM
  4. customthe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b3ffbd97c704f95bdf6f0a60b1598c2
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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