Triphenylphosphine → HCID 15391551, compound

HRID 54020Notes

Reaction equation

[Si:1]([O:18][CH2:19][CH:20]([CH2:24][CH2:25][CH2:26][Br:27])[CH2:21][CH2:22][Br:23])([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(C(O[SiH](C1C=CC=CC=1)C1C=CC=CC=1)[C@@H](CCCO)CCO)(C)(C)C.BrN1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[Si:1]([O:18][CH2:19][C@@H:20]([CH2:24][CH2:25][CH2:26][Br:27])[CH2:21][CH2:22][Br:23])([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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 67184N-bromobutanimide

HCID 187904553-(Tert-butyldiphenylsilyloxymethyl)-1,6-dibromohexane

HCID 131719532HCID 131719532, compound

Product 1

HCID 15391551HCID 15391551, compoundYield 75%

Procedure

Following the same procedure described for the preparation of racemic dibromide, 3-(tert-butyldiphenylsilyloxymethyl)-1,6-dibromohexane, (S)-(-)-3-(tertbutyldiphenylsilyloxymethyl)-1,6-hexanediol (4.85 g, 12.53 mmol) was reacted with N-bromosuccinimide (5.35 g, 30.1 mmol) and triphenylphosphine (7.87 g, 30.1 mmol) CH2Cl2 (150 mL) at 0° C. to afford compound (S)-(-)-3-(tert-butyldiphenylsilyloxymethyl)-1,6-dibromohexane 4.81 (75%) as a clear, colorless oil which was homogenous by TLC (Rf =0.8, 10% EtOAc in hexanes. Both the TLC properties and 1H spectra of this compound were identical in all respects with racemic isomer. MS.

Sources & evidence

ORD record: ord-2f23f0b2fd174a2998930669b3ae2887
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05621098

Reaction notes

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