9-Iodo-9-borabicyclo(3.3.1)nonane → 7-t-Butyl-5-[ethyl-(4-hydroxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran

HRID 2290157Notes

Reaction equation

HRID 2290157 reaction equation
[C:1]([C:5]1[C:13]2[O:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N:16]([CH2:25][CH3:26])[C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)[C:6]=1[CH3:27])([CH3:4])([CH3:3])[CH3:2].IB1C2CCCC1CCC2>ClCCl>[C:1]([C:5]1[C:13]2[O:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N:16]([CH2:25][CH3:26])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:6]=1[CH3:27])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 5782319-Iodo-9-borabicyclo(3.3.1)nonaneHCID 186991837-t-Butyl-5-[ethyl-(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran2×

Product 1

HCID 186991937-t-Butyl-5-[ethyl-(4-hydroxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following general procedure M and using 7-t-butyl-5-[ethyl-(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 56, 0.12 g, 0.3 mmol) and 1M solution of 9-iodo-9-borabicyclo[3.3.1]nonane (B-iodo-9-BBN) in hexanes (0.44 mL, 0.44 mmol) in 2 mL of anhydrous dichloromethane, the title compound was obtained as a brown oil that was used in the next step without further purification.

Sources & evidence

ORD record
ord-c98ac4e7ca17475f972f3abd9d8e8916
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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