Water → HCID 22594215, compound

HRID 1761011Notes

Reaction equation

HRID 1761011 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].FC1C=C(C=CC=1)C[O:12][C:13](=O)[C:14]1[C:15](=[CH:27][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)=[CH:29][CH:30]=1)[C:16](OCC1C=CC=C(F)C=1)=[O:17].O.S(=O)(=O)(O)O>C(OCC)C>[F:39][C:35]1[CH:34]=[C:33]([CH:38]=[CH:37][CH:36]=1)[CH2:32][O:31][C:28]1[CH:29]=[CH:30][C:14]([CH2:13][OH:12])=[C:15]([CH2:16][OH:17])[CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 69781516HCID 69781516, compound

Product 1

HCID 22594215HCID 22594215, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (2.15 g, 56.9 mmol) and diethyl ether (150 mL) at 0° C. a solution of 4-(3-fluoro-benzyloxy)-phthalic acid bis-(3-fluoro-benzyl) ester (13.1 g, 25.9 mmol) in diethyl ether (150 mL) was added over 1 h. After a further 1.5 h water (100 mL) and sulfuric acid (2 M, 100 mL) was added and the resulting mixture was extracted with diethyl ether (2×100 mL). The combined extracts were then dried over sodium sulfate, filtered and evaporated to leave a clear oil which was purified by chromatography (SiO2, hexane:ethyl acetate 1:1 to 2:3) to afford the title product (5.1 g, 76%) as a white solid. MS m/e=260.6 (M+H+).

Workup

  1. additionwas added over 1 h
  2. extractionthe resulting mixture was extracted with diethyl ether (2×100 mL)
  3. dry with materialThe combined extracts were then dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto leave a clear oil which
  7. customwas purified by chromatography (SiO2, hexane:ethyl acetate 1:1 to 2:3)

Sources & evidence

ORD record
ord-faf8562f4f9e4c46a7702f9d1397b70c
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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