Ethyl bromoacetate → HCID 19761562, compound

HRID 654551Notes

Reaction equation

HRID 654551 reaction equation
C1C2C(=CC=CC=2)C=CC=1COC1C=C(C=CC=1)C=O.BrCC(OCC)=O.[OH:28][CH:29]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH2:43][C:44]2[CH:53]=[CH:52][C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:45]=2)[CH:37]=1)[CH2:30][C:31](OCC)=[O:32].[H-].[Al+3].[Li+].[H-].[H-].[H-]>[Zn]>[CH:45]1[C:46]2[C:51](=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:52]=[CH:53][C:44]=1[CH2:43][O:42][C:38]1[CH:37]=[C:36]([CH:29]([OH:28])[CH2:30][CH2:31][OH:32])[CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 10753946HCID 10753946, compoundHCID 19761541HCID 19761541, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19761562HCID 19761562, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A mixture of 3-(naphth-2-ylmethoxy)benzaldehyde, ethyl bromoacetate and zinc was reacted using the procedure described in Example 2. There was thus obtained ethyl 3-hydroxy-3-[3-(naphth-2-ylmethoxy)phenyl)propionate which was reduced with lithium aluminium hydride using the conditions described in note d above to give 3-[3-(naphth-2-ylmethoxy)phenyl]propane-1,3-diol as a colourless oil.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-a19624342dbf4894bbac717082d47336
Source dataset
uspto-grants-1992_07
Patent number
US05132328

Reaction notes

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