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1,7-Diphenyl-4-heptanol → 1-(4-tert-Butyldiphenylsilyloxymethylphenyl)-7-phenyl-heptan-4-ol

HRID 892
Notes
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Reaction equation

HRID 892 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH:29]=[O:30])=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]1([CH2:37][CH2:38][CH2:39][Mg]Br)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1(CCCC(O)CCCC2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH:29]([OH:30])[CH2:39][CH2:38][CH2:37][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:22][CH:21]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 105398701,7-Diphenyl-4-heptanolHCID 196941314-(4-tert-Butyldiphenylsilyloxymethyl-phenyl)butyraldehydeHCID 178418471HCID 178418471, compound

Product 1

HCID 196941361-(4-tert-Butyldiphenylsilyloxymethylphenyl)-7-phenyl-heptan-4-olYield 122.9%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

The alcohol 173 was prepared from 2.12 g (5.0 mmol) of 172 and 9.0 mL (9 mmol) of 120 in 50 mL of THF as described for the synthesis of 121 in Example 1. Flash chromatography (elution with 10% ethyl acetate in hexane) gave 3.3 g of the alcohol 173. 1H NMR consistent with the product.

Workup

  1. washFlash chromatography (elution with 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-796ad571c9a54fe982b77146ea41a2af
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723459

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes