Disiloxane → 2-Phenyl-1-propanol

HRID 1582414Notes

Reaction equation

[SiH3]O[SiH3].[C:4]1([C@H:10]([CH3:13])[CH2:11][OH:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>>[C:4]1([CH:10]([CH3:13])[CH2:11][OH:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 123318Disiloxane

HCID 4476612-Phenylpropanol

Product 1

HCID 142952-Phenyl-1-propanol

Procedure

Furthermore, the purificative deprotections of the chiral silylethers (1f and 1m) were examined in the presence of the corresponding enantiomerically pure alcohols using the triphasic system of FIGS. 2 and 3. The deprotection reaction of 1f (1.0 equiv) proceeded in the presence of (R)-(+)-1-(2-naphthyl)ethanol (1.0 equiv), and 1-(2-naphthyl)ethanol was obtained in 83% total yield in a ratio with 41/59 in P-/S-phases (entry 5). The enantiomeric excess (ee) values of 1-(2-naphthyl)ethanol obtained were >97% and 90% in P- and S-phases, respectively. The chiral silyl ether 1m (1.0 equiv) also underwent the purificative deprotection in the presence of (S)-(−)-2-phenylpropanol (1.0 equiv), and 2-phenylpropanol was obtained in 76% total yield in a ratio with 39/61 in P/S-phases. The ee values of 2-phenylpropanol were 89% and 87% in P- and S-phases, respectively.

Sources & evidence

ORD record: ord-e44f2f8a47204165912c0d72df340a1d
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734318B2

Reaction notes

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