Water → Diphenylmethyl [3-fluoro-4,5-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]-hydroxy-acetate

HRID 2574

Reaction equation

HRID 2574 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]([OH:26])[C:23]([OH:25])=[O:24])[CH:5]=[C:6]([O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:7]=1[O:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14].[C:27]1([C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N+]=[N-])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>ClCCl.CCOCC>[F:1][C:2]1[CH:3]=[C:4]([CH:22]([OH:26])[C:23]([O:25][CH:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:24])[CH:5]=[C:6]([O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:7]=1[O:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 9951689[3-Fluoro-4,5-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]-hydroxy-acetic acid

Product 1

HCID 9915375Diphenylmethyl [3-fluoro-4,5-bis-[(2-methoxy-ethoxy)-methoxy]-phenyl]-hydroxy-acetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

5.3 g of the acid of Step A were dissolved in 66 ml of dichloromethane and then 46 ml of a solution of diphenyl diazomethane at 6.5 g in ether were added at 15° C. The mixture was stirred for 16 hours at ambient temperature and then water was added, followed by decanting and acidifying with acetic acid. Washing with a saturated solution of sodium bicarbonate, drying and evaporating the solvents yielded after chromatography on silica and eluting with an ethyl acetate--hexane mixture (50--50) 4.0 g of the desired product with a Rf=0.17.

Workup

  1. customby decanting
  2. washWashing with a saturated solution of sodium bicarbonate
  3. customdrying
  4. customevaporating the solvents
  5. customyielded after chromatography on silica
  6. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-5043e9c099ff4fda98d9234332a5cc3e
Source dataset
uspto-grants-1998_03
Patent number
US05728828

Linked notes

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