Methanol → (3-(4-(tert-Butyldimethylsilyloxy)but-1-ynyl)phenyl)methanol

HRID 1255265Notes

Reaction equation

HRID 1255265 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11]O)[CH:6]=[CH:7][CH:8]=1.[C:13]([Si:17]([CH3:24])([CH3:23])[O:18][CH2:19]CC#C)([CH3:16])([CH3:15])[CH3:14].CO>N>[Si:17]([O:18][CH2:19][CH2:11][C:10]#[C:9][C:5]1[CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=[CH:7][CH:6]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilaneHCID 552676803-(3-(Hydroxymethyl)phenyl)propan-1-ol

Product 1

HCID 58168614(3-(4-(tert-Butyldimethylsilyloxy)but-1-ynyl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

Prepared by the method of Aromatic Intermediate 18, step a using tert-butyldimethyl(but-3-ynyloxy)silane (0.92 g) in place of tert-butyldimethyl(prop-2-ynyloxy)silane. The preparative HPLC conditions were changed to XBridge™, Gradient: 75-99% methanol in 0.2% aqueous ammonia to avoid cleavage of the silyl protecting group. Yield 0.79 g.

Sources & evidence

ORD record
ord-9d5dc419da804c37b93b1265af03f15b
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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