Hydrochloric Acid → HCID 15595179, compound

HRID 1906210Notes

Reaction equation

HRID 1906210 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1([CH3:29])[CH2:19][C:18](=[O:20])[C:17]2[CH:21]=[CH:22][C:23]([OH:28])=[C:24]([CH2:25][CH2:26][CH3:27])[C:16]=2[O:15]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][C:38]([O:40][CH3:41])=[O:39].Cl>CCOCC.O.CN(C)C=O>[CH3:41][O:40][C:38](=[O:39])[CH2:37][O:28][C:23]1[CH:22]=[CH:21][C:17]2[C:18](=[O:20])[CH2:19][C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)([CH3:29])[O:15][C:16]=2[C:24]=1[CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 15595178HCID 15595178, compound

Product 1

HCID 15595179HCID 15595179, compoundYield 70.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.706 g of rac.-2,3-dihydro-2-[6-[(tetrahydro-2H-pyran-2-yl)oxy]hexyl]-7-hydroxy-2-methyl-8-propyl-4H-1-benzopyran-4-one, 16 ml of N,N-dimethylformamide, and 0.477 g of anhydrous potassium carbonate was stirred at room temperature for 2 hours. A 0.33 ml (0.53 g) portion of methyl bromoacetate was added and stirring was continued for 17.5 hours at room temperature. The mixture was poured into water and the pH was adjusted to 7 with 0.5N hydrochloric acid. The organic product was isolated by extraction with 3 portions of ether. The ether extracts were combined, washed with water and brine, dried over anhydrous magnesium sulfate filtered and concentrated in vacuo to give a yellow oil. This material was purified by high pressure liquid chromatography (HPLC) (silica gel, 2:1 hexane-ethyl acetate) yielding 0.589 g (70.8%) of rac.-[[3,4-dihydro-2-[6-[(tetrahydro-2H-pyran-2-yl)oxy]hexyl]-2-methyl-4-oxo-8-propyl-2H-1-benzopyran-7-yl]oxy]acetic acid methyl ester as a pale-yellow oil.

Workup

  1. stirringstirring
  2. waitwas continued for 17.5 hours at room temperature
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThis material was purified by high pressure liquid chromatography (HPLC) (silica gel, 2:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b4e912dfcb6e46548cd8cc7048a525aa
Source dataset
uspto-grants-1987_03
Patent number
US04650812

Reaction notes

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